N-benzyloxycarbonyl-3-pyrrolidinone_properties by Asch

Query Query

Results

Date

204 substances in Reaxys

2017-11-12 20h:27m:54s (EST)

1. Query

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Reaxys ID 1460858 View in Reaxys

1/204 CAS Registry Number: 96658-35-4 Chemical Name: N-(benzyloxycarbonyl)pyrrol-2(5H)-one; 2oxo-2,5-dihydro-pyrrole-1-carboxylic acid benzyl ester; N-Benzyloxycarbonyl-2-oxo-Δ3-pyrrolin Linear Structure Formula: C12H11NO3 Molecular Formula: C12H11NO3 Molecular Weight: 217.224 Type of Substance: heterocyclic InChI Key: HERZGTHCKVCGSP-UHFFFAOYSA-N Note:

O N

Substance Label (3) Label References 8

Mattern, Ralph-Heiko; Tetrahedron Letters; vol. 37; nb. 3; (1996); p. 291 - 294, View in Reaxys

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys

Cox et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 1539,1543, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.67

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

89 - 90

Solvent (Melting Point)

diisopropyl ether

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Curti, Claudio; Ranieri, Beatrice; Battistini, Lucia; Rassu, Gloria; Zambrano, Vincenzo; Pelosi, Giorgio; Casiraghi, Giovanni; Zanardi, Franca; Advanced Synthesis and Catalysis; vol. 352; nb. 11-12; (2010); p. 2011 - 2022, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Cox et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 1539,1543, View in Reaxys

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

2/232

2017-11-12 20:29:58

Curti, Claudio; Ranieri, Beatrice; Battistini, Lucia; Rassu, Gloria; Zambrano, Vincenzo; Pelosi, Giorgio; Casiraghi, Giovanni; Zanardi, Franca; Advanced Synthesis and Catalysis; vol. 352; nb. 11-12; (2010); p. 2011 2022, View in Reaxys 2 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys; Mattern, Ralph-Heiko; Tetrahedron Letters; vol. 37; nb. 3; (1996); p. 291 - 294, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Mattern, Ralph-Heiko; Tetrahedron Letters; vol. 37; nb. 3; (1996); p. 291 - 294, View in Reaxys 5 of 5

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys; Mattern, Ralph-Heiko; Tetrahedron Letters; vol. 37; nb. 3; (1996); p. 291 - 294, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1765 - 1650 cm**(-1)

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys

Reaxys ID 1533956 View in Reaxys

2/204

3/232

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CAS Registry Number: 14468-80-5 Chemical Name: N-benzyloxycarbonylpyrrolidin-2-one; NCbz-2-pyrrolidinone; 2-oxo-pyrrolidine-1-carboxylic acid benzyl ester; 1-(benzyloxycarbonyl)-1-azacyclopentan-2-one; 1-(benzyloxycarbonyl)pyrrolidin-2-one; N-(benzyloxycarbonyl)pyrrolidin-2-one; benzyl 2-oxopyrrolidine-1-carboxylate Linear Structure Formula: C12H13NO3 Molecular Formula: C12H13NO3 Molecular Weight: 219.24 Type of Substance: heterocyclic InChI Key: DVMZKGUWEAXMRT-UHFFFAOYSA-N Note:

O N

Substance Label (12) Label References 1

Arizpe, Alicia; Rodríguez-Mata, María; Sayago, Francisco J.; Pueyo, María J.; Gotor, Vicente; Jiménez, Ana I.; Gotor-Fernández, Vicente; Cativiela, Carlos; Tetrahedron Asymmetry; vol. 26; nb. 24; (2015); p. 1469 - 1477, View in Reaxys

Louwrier, Saskia; Tuynman, Antonin; Hiemstra, Henk; Tetrahedron; vol. 52; nb. 7; (1996); p. 2629 - 2646, View in Reaxys; Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys

Tab.1.col.2.run 10 Lu, Yuhua; Taylor, Richard T.; Heterocycles; vol. 62; (2004); p. 869 - 876, View in Reaxys Table 2, entry 2, n Tsujimoto, Takashi; Murai, Akio; Synlett; nb. 8; (2002); p. 1283 - 1284, View in Reaxys =1 3

Muramatsu et al.; Chemistry Letters; (1977); p. 1253,1254,1255, View in Reaxys; Peroche, Sandrine; Remuson, Roland; Gelas-Mialhe, Yvonne; Gramain, Jean-Claude; Tetrahedron Letters; vol. 42; nb. 28; (2001); p. 4617 - 4619, View in Reaxys

Gibbs, Gary; Hateley, Martin J.; McLaren, Lee; Welham, Matthew; Willis, Christine L.; Tetrahedron Letters; vol. 40; nb. 5; (1999); p. 1069 - 1072, View in Reaxys

Oliveira, Denilson F.; Miranda, Paulo C. M. L.; Correia, Carlos R. D.; Journal of Organic Chemistry; vol. 64; nb. 18; (1999); p. 6646 - 6652, View in Reaxys

Marais, Wilhelmina; Holzapfel, Cedric W.; Synthetic Communications; vol. 28; nb. 19; (1998); p. 3681 3691, View in Reaxys

Wei, Zhong-Yong; Knaus, Edward E.; Tetrahedron Letters; vol. 35; nb. 6; (1994); p. 847 - 848, View in Reaxys

Giovannini, Arianna; Savoia, Diego; Umani-Ronchi, Achille; Journal of Organic Chemistry; vol. 54; nb. 1; (1989); p. 228 - 234, View in Reaxys

Nagasaka, Tatsuo; Tamano, Hirohisa; Hamaguchi, Fumiko; Heterocycles; vol. 24; nb. 5; (1986); p. 1231 1232, View in Reaxys

Rothe,M.; Toth,T.; Chemische Berichte; vol. 99; (1966); p. 3820 - 3829, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.581

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

36 - 37

4/232

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Melting Point [°C]

34 - 36

Giovannini, Arianna; Savoia, Diego; Umani-Ronchi, Achille; Journal of Organic Chemistry; vol. 54; nb. 1; (1989); p. 228 - 234, View in Reaxys Boiling Point (1) Boiling Point [°C] 147

Pressure (Boiling Point) [Torr]

References

0.1

Rothe,M.; Toth,T.; Chemische Berichte; vol. 99; (1966); p. 3820 - 3829, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5462

Rothe,M.; Toth,T.; Chemische Berichte; vol. 99; (1966); p. 3820 3829, View in Reaxys

Location

References

589

Chromatographic Data (1) Chromatographic Original string data LC (Liquid chromatography)

silica gel amount: Paragraph 0304 150 g, eluent: nhexane/ethyl acetate=1/1, Rf=0.45

Crystal Property Description (6) Colour & Other Location Properties colourless

Paragraph 0304

Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys

References Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys

white

colourless

Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo; Tetrahedron; vol. 67; nb. 40; (2011); p. 7829 - 7837, View in Reaxys

yellow

supporting information

Piperno, Anna; Carnovale, Caterina; Giofr, Salvatore V.; Iannazzo, Daniela; Tetrahedron Letters; vol. 52; nb. 51; (2011); p. 6880 - 6882, View in Reaxys

white

supporting information

colorless

Patent; UNIVERSITA' DEGLI STUDI DI TRIESTE; WO2005/123067; (2005); (A1) English, View in Reaxys

NMR Spectroscopy (14) 1 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR

(300 MHz, CDCl3, TMS) δ 1.94-2.04 (m, 2H), 2.49 (t, J=8.1 Hz, 2H), 3.78 (t, J=7.1 Hz, 2H), 5.24 (s, 2H), 7.30-7.42 (m, 5H).

Location

Paragraph 0304

Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys

5/232

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2 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Original Text (NMR Spectroscopy)

13C-NMR

Location

Paragraph 0304

(75 MHz, CDCl3, CDCl3) δ 17.05, 32.27, 45.96, 67.33, 127.68, 127.90, 128.13, 135.06, 150.98, 173.63.

Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys 3 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo; Tetrahedron; vol. 67; nb. 40; (2011); p. 7829 7837, View in Reaxys 4 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo; Tetrahedron; vol. 67; nb. 40; (2011); p. 7829 7837, View in Reaxys 5 of 14

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Piperno, Anna; Carnovale, Caterina; Giofr, Salvatore V.; Iannazzo, Daniela; Tetrahedron Letters; vol. 52; nb. 51; (2011); p. 6880 - 6882, View in Reaxys 6 of 14

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

6/232

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Location

supporting information

Piperno, Anna; Carnovale, Caterina; Giofr, Salvatore V.; Iannazzo, Daniela; Tetrahedron Letters; vol. 52; nb. 51; (2011); p. 6880 - 6882, View in Reaxys 7 of 14

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

200

Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys 8 of 14

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

50.3

Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys 9 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

200

Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys 10 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

24.84

Frequency (NMR Spectroscopy) [MHz]

50.3

Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys 11 of 14

Description (NMR Spec- Chemical shifts troscopy)

7/232

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Giovannini, Arianna; Savoia, Diego; Umani-Ronchi, Achille; Journal of Organic Chemistry; vol. 54; nb. 1; (1989); p. 228 - 234, View in Reaxys; Louwrier, Saskia; Tuynman, Antonin; Hiemstra, Henk; Tetrahedron; vol. 52; nb. 7; (1996); p. 2629 - 2646, View in Reaxys 12 of 14

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Louwrier, Saskia; Tuynman, Antonin; Hiemstra, Henk; Tetrahedron; vol. 52; nb. 7; (1996); p. 2629 - 2646, View in Reaxys 13 of 14

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Louwrier, Saskia; Tuynman, Antonin; Hiemstra, Henk; Tetrahedron; vol. 52; nb. 7; (1996); p. 2629 - 2646, View in Reaxys 14 of 14

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

Muramatsu et al.; Chemistry Letters; (1977); p. 1253,1254,1255, View in Reaxys IR Spectroscopy (6) 1 of 6

Description (IR Spectroscopy)

Bands

Original Text (IR Spectroscopy)

IR (liquid film) 3063 (uCH(Ar), 2982-2895 (uCH), 1788-1717 (uC═O), 1383 (δCH), 1240 (uC—O).

Location

Paragraph 0304

Comment (IR Spectroscopy)

film

Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys 2 of 6

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo; Tetrahedron; vol. 67; nb. 40; (2011); p. 7829 7837, View in Reaxys 3 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys 4 of 6

Description (IR Spectroscopy)

Bands

8/232

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Solvent (IR Spectroscopy)

CDCl3

Comment (IR Spectroscopy)

3020 - 1715 cm**(-1)

Louwrier, Saskia; Tuynman, Antonin; Hiemstra, Henk; Tetrahedron; vol. 52; nb. 7; (1996); p. 2629 - 2646, View in Reaxys 5 of 6

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

1785 - 1720 cm**(-1)

Giovannini, Arianna; Savoia, Diego; Umani-Ronchi, Achille; Journal of Organic Chemistry; vol. 54; nb. 1; (1989); p. 228 - 234, View in Reaxys 6 of 6

Description (IR Spectroscopy)

Muramatsu et al.; Chemistry Letters; (1977); p. 1253,1254,1255, View in Reaxys Mass Spectrometry (4) Description (Mass Location Spectrometry) electrospray ionisation (ESI); spectrum

References

Paragraph 0304

Patent; Yamano, Mitsuhisa; Yamada, Masatoshi; Usutani, Hirotsugu; US2015/51416; (2015); (A1) English, View in Reaxys

ESI (Electrospray ionisation); HRMS (High resolution mass spectrometry); Spectrum

Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo; Tetrahedron; vol. 67; nb. 40; (2011); p. 7829 - 7837, View in Reaxys

ESI (Electrospray ionisation); Spectrum

Huang, Wei; Ma, Jing-Yi; Yuan, Mu; Xu, Long-Fei; Wei, Bang-Guo; Tetrahedron; vol. 67; nb. 40; (2011); p. 7829 - 7837, View in Reaxys

spectrum

Giovannini, Arianna; Savoia, Diego; Umani-Ronchi, Achille; Journal of Organic Chemistry; vol. 54; nb. 1; (1989); p. 228 - 234, View in Reaxys; Guenin, Erwann; Monteil, Maelle; Bouchemal, Nadia; Prange, Thierry; Lecouvey, Marc; European Journal of Organic Chemistry; nb. 20; (2007); p. 3380 - 3391, View in Reaxys

Reaxys ID 5432076 View in Reaxys

3/204 CAS Registry Number: 130312-02-6 Chemical Name: benzyl 3-oxopyrrolidine-1-carboxylate; N(benzyloxycarbonyl)-3-pyrrolidinone; benzyl 3-oxo-1-pyrrolidine carboxylate; N-(Benzyloxycarbonyl)pyrrolidin-3-one; benzyl pyrrolidin-3-one-1-carboxylate; N-benzyloxycarbonyl-pyrrolidin-3one; N-benzyloxycarbonyl-3-pyrrolidinone Linear Structure Formula: C12H13NO3 Molecular Formula: C12H13NO3 Molecular Weight: 219.24 Type of Substance: heterocyclic InChI Key: LMHWEUQNJRXMCD-UHFFFAOYSA-N Note:

O N

Substance Label (14) Label References 229-1

Patent; GUANGDONG ZHONGSHENG PHARMACEUTICAL CO., LTD; WU, Hao; LIN, Jun; LI, Yunhui; WEI, Changqing; CHEN, Shuhui; LONG, Chaofeng; CHEN, Xiaoxin; LIU, Zhuowei; CHEN, Lijuan; (212 pag.); EP3124482; (2017); (A1) English, View in Reaxys

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Li, Chao; Liu, Yan; Pei, Xiao-Qiong; Wu, Zhong-Liu; Process Biochemistry; vol. 56; (2017); p. 90 - 97, View in Reaxys

Kusumi, Kensuke; Shinozaki, Koji; Yamaura, Yoshiyuki; Hashimoto, Ai; Kurata, Haruto; Naganawa, Atsushi; Otsuki, Kazuhiro; Matsushita, Takeshi; Sekiguchi, Tetsuya; Kakuuchi, Akito; Yamamoto, Hiroshi; Seko, Takuya; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 4; (2016); p. 1209 - 1213, View in Reaxys

Patent; YM BIOSCIENCES AUSTRALIA PTY LTD; BURNS, Christopher John; WO2014/32; (2014); (A1) English, View in Reaxys

Patent; HUA MEDICINE (SHANGHAI) LTD.; CHEN, Li; BALDWIN, John J.; WU, Chengde; SHEN, Chunli; WO2014/124560; (2014); (A1) English, View in Reaxys

6.iv

Patent; ACTELION PHARMACEUTICALS LTD; WO2008/56335; (2008); (A1) English, View in Reaxys; Patent; Actelion Pharmaceuticals Ltd.; US2009/247578; (2009); (A1) English, View in Reaxys

Patent; SCHERING CORPORATION; WO2009/105500; (2009); (A1) English, View in Reaxys

Plouvier, Bertrand; Beatch, Gregory N.; Jung, Grace L.; Zolotoy, Alexander; Sheng, Tao; Clohs, Lilian; Barrett, Terrance D.; Fedida, David; Wang, Wei Q.; Zhu, Jeff J.; Liu, Yuzhong; Abraham, Shlomo; Lynn, Leah; Dong, Ying; Wall, Richard A.; Walker, Michael J. A.; Journal of Medicinal Chemistry; vol. 50; nb. 12; (2007); p. 2818 - 2841, View in Reaxys

12d

Luo, Juntao; Pardin, Christophe; Lubell, William D.; Zhu; Chemical Communications; nb. 21; (2007); p. 2136 - 2138, View in Reaxys

Patent; PFIZER PRODUCTS INC.; WO2007/60526; (2007); (A1) English, View in Reaxys

V-1

Patent; GLAXO GROUP LIMITED; WO2006/2047; (2006); (A2) English, View in Reaxys

Caldwell, Charles G.; Chen, Ping; He, Jiafang; Parmee, Emma R.; Leiting, Barbara; Marsilio, Frank; Patel, Reshma A.; Wu, Joseph K.; Eiermann, George J.; Petrov, Aleksandr; He, Huaibing; Lyons, Kathryn A.; Thornberry, Nancy A.; Weber, Ann E.; Bioorganic and Medicinal Chemistry Letters; vol. 14; nb. 5; (2004); p. 1265 - 1268, View in Reaxys

Wang, Jianbo; Hou, Yihua; Wu, Peng; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2277 - 2280, View in Reaxys

Cooper, Curt S.; Klock, Pamela L.; Chu, Daniel T. W.; Hardy, Dwight J.; Swanson, Robert N.; Plattner, Jacob J.; Journal of Medicinal Chemistry; vol. 35; nb. 8; (1992); p. 1393 - 1398, View in Reaxys

Druglikeness (1) 1 of 1

LogP

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Original string data

Location

References

TLC (Thin layer chromatography)

Page/Page column 52

Patent; YM BIOSCIENCES AUSTRALIA PTY LTD; BURNS, Christopher John; WO2014/32; (2014); (A1) English, View in Reaxys

TLC:Rf=0.7(silica gel,EA:PE=1 : 1 , v/v)

Crystal Property Description (5) Colour & Other Location Properties

References

colourless

supporting information

Cabrera-Pardo, Jaime R.; Trowbridge, Aaron; Nappi, Manuel; Ozaki, Kyohei; Gaunt, Matthew J.; Angewandte Chemie - International Edition; vol. 56; nb. 39; (2017); p. 11958 - 11962; Angew. Chem.; vol. 129; nb. 39; (2017); p. 12120 - 12124,5, View in Reaxys

yellow

Page/Page column 52

Patent; YM BIOSCIENCES AUSTRALIA PTY LTD; BURNS, Christopher John; WO2014/32; (2014); (A1) English, View in Reaxys

light-yellow

Patent; ACTELION PHARMACEUTICALS LTD; WO2008/56335; (2008); (A1) English, View in Reaxys; Patent; Actelion Pharmaceuticals Ltd.; US2009/247578; (2009); (A1) English, View in Reaxys

10/232

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colorless

Page/Page column 126

orange

Patent; Bristol-Myers Squibb Company; US2007/161685; (2007); (A1) English, View in Reaxys Patent; MERCK and CO., INC.; WO2005/44195; (2005); (A2) English, View in Reaxys; Patent; MERCK and CO., INC.; WO2004/43940; (2004); (A1) English, View in Reaxys; Patent; MERCK and CO., INC.; WO2005/108382; (2005); (A1) English, View in Reaxys; Patent; MERCK and CO., INC.; WO2005/116029; (2005); (A1) English, View in Reaxys

NMR Spectroscopy (13) 1 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

1H NMR (DMSO ; δ ppm): 2.48-2.61 (2H, m); 3.61-3.80 (4H, m); 5.09 (2H, s); 7.27-7.41 d6 (5H, m)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

2.48 - 2.61; 3.61 - 3.8; 5.09; 7.27 - 7.41

Kind of signal

2H, m; 4H, m; 2H, s; 5H, m

Patent; Actelion Pharmaceuticals Ltd.; US2009/247578; (2009); (A1) English, View in Reaxys 3 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Original Text (NMR Spectroscopy)

NMR (DMSOd6; δ ppm): 2.48-2.61 (2H, m); 3.61-3.80 (4H, m); 5.09 (2H, s); 7.27-7.41 (5H, m).

Comment (NMR Spectroscopy)

Signals given

Patent; ACTELION PHARMACEUTICALS LTD; WO2008/56335; (2008); (A1) English, View in Reaxys 4 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Cooper, Curt S.; Klock, Pamela L.; Chu, Daniel T. W.; Hardy, Dwight J.; Swanson, Robert N.; Plattner, Jacob J.; Journal of Medicinal Chemistry; vol. 35; nb. 8; (1992); p. 1393 - 1398, View in Reaxys; Luo, Juntao; Pardin, Christophe; Lubell, William D.; Zhu; Chemical Communications; nb. 21; (2007); p. 2136 - 2138, View in Reaxys 7 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- tetradeuteriomethanol scopy) Luo, Juntao; Pardin, Christophe; Lubell, William D.; Zhu; Chemical Communications; nb. 21; (2007); p. 2136 2138, View in Reaxys 8 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

NMR (CDCI3) δ 7.34-7.28 (m, 5H), 5.14 (s, 2H), 3.83-3.78 (m, 4H), 2.56 (t, J = 7.9 Hz, 2H).

Comment (NMR Spectroscopy)

Signals given

Patent; PFIZER PRODUCTS INC.; WO2007/60526; (2007); (A1) English, View in Reaxys 9 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR (300 MHz, CDCl3) δ: 2.61 (2H, t, J=7.5 Hz), 3.83-3.89 (4H, m), 5.18 (2H, s), 7.33-7.39 (5H, m)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

2.61; 3.83 - 3.89; 5.18; 7.33 - 7.39

Kind of signal

2H, t, J=7.5 Hz; 4H, m; 2H, s; 5H, m

Patent; Takeda Pharmaceutical Company Limited; EP1553074; (2005); (A1) English, View in Reaxys 10 of 13

Description (NMR Spec- Chemical shifts troscopy)

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Nucleus (NMR Spectroscopy)

13C

Frequency (NMR Spectroscopy) [MHz]

Wang, Jianbo; Hou, Yihua; Wu, Peng; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2277 - 2280, View in Reaxys 11 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

200

Wang, Jianbo; Hou, Yihua; Wu, Peng; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2277 - 2280, View in Reaxys 12 of 13

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Frequency (NMR Spectroscopy) [MHz]

200

Wang, Jianbo; Hou, Yihua; Wu, Peng; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2277 - 2280, View in Reaxys 13 of 13

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Cooper, Curt S.; Klock, Pamela L.; Chu, Daniel T. W.; Hardy, Dwight J.; Swanson, Robert N.; Plattner, Jacob J.; Journal of Medicinal Chemistry; vol. 35; nb. 8; (1992); p. 1393 - 1398, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Wang, Jianbo; Hou, Yihua; Wu, Peng; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2277 - 2280, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry)

Comment (Mass Spectrometry)

liquid chromatog- Page/Page colraphy mass spec- umn 52; 73 trometry (LCMS); electron impact (EI); spectrum LCMS (Liquid chromatography mass spectrome-

Page/Page column 126

References Patent; YM BIOSCIENCES AUSTRALIA PTY LTD; BURNS, Christopher John; WO2014/32; (2014); (A1) English, View in Reaxys

Molecular peak

Patent; Bristol-Myers Squibb Company; US2007/161685; (2007); (A1) English, View in Reaxys

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try); ESI (Electrospray ionisation) spectrum; electron impact (EI)

Wang, Jianbo; Hou, Yihua; Wu, Peng; Journal of the Chemical Society - Perkin Transactions 1; nb. 16; (1999); p. 2277 - 2280, View in Reaxys

Reaxys ID 7534788 View in Reaxys

4/204 Linear Structure Formula: C12H11NO4 Molecular Formula: C12H11NO4 Molecular Weight: 233.224 Type of Substance: heterocyclic InChI Key: PQPKPBMAURELDK-UHFFFAOYSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

0.531

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Related Structure (1) Related Structure Referenced Com- References pound The following tautomers are discussed: /BRN= 7534789/

4-hydroxy-2Hamilakis; Kontonassios; Sandris; Journal of Heterocyclic Chemistry; vol. 33; nb. 3; oxo-3-pyrroline-1- (1996); p. 825 - 829, View in Reaxys carboxylic acid benzyl ester

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Hamilakis; Kontonassios; Sandris; Journal of Heterocyclic Chemistry; vol. 33; nb. 3; (1996); p. 825 - 829, View in Reaxys

Reaxys ID 18936961 View in Reaxys

5/204 CAS Registry Number: 1030899-57-0 Chemical Name: benzyl (2S)-2-methyl-3-oxopyrrolidine-1-carboxylate Linear Structure Formula: C13H15NO3 Molecular Formula: C13H15NO3 Molecular Weight: 233.267 InChI Key: SXRCSLUPXCTDRP-JTQLQIEISA-N Note:

N O

Substance Label (2)

14/232

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Label

References

Asano, Moriteru; Hitaka, Takenori; Imada, Takashi; Yamada, Masami; Morimoto, Megumi; Shinohara, Hiromi; Hara, Takahito; Yamaoka, Masuo; Santou, Takashi; Nakayama, Masaharu; Imai, Yumi; Habuka, Noriyuki; Yano, Jason; Wilson, Keith; Fujita, Hisashi; Hasuoka, Atsushi; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 9; (2017); p. 1897 - 1901, View in Reaxys

Yamamoto, Satoshi; Kobayashi, Hiromi; Kaku, Tomohiro; Aikawa, Katsuji; Hara, Takahito; Yamaoka, Masuo; Kanzaki, Naoyuki; Hasuoka, Atsushi; Baba, Atsuo; Ito, Mitsuhiro; Bioorganic and Medicinal Chemistry; vol. 21; nb. 1; (2013); p. 70 - 83, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.526

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Crystal Property Description (2) Colour & Other References Properties yellow

colorless

Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCl ) δ: 1.34 (3H, d, J = 6.6 Hz), 2.50-2.70 (2H, m), 3.60-3.75 (1H, 3 m), 3.90-4.10 (2H, m), 5.15 (1H, d, J = 12.3 Hz), 5.20 (1H, d, J = 12.3 Hz), 7.30-7.40 (5H, m)

Signals [ppm]

1.34; 2.5 - 2.7; 3.6 - 3.75; 3.9 - 4.1; 5.15; 5.2; 7.3 - 7.4

Kind of signal

3H, d, J = 6.6 Hz; 2H, m; 1H, m; 2H, m; 1H, d, J = 12.3 Hz; 1H, d, J = 12.3 Hz; 5H, m

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

1H-NMR(CDCl )δ:1.34(3H,d,J=6.6 Hz), 2.50-2.70(2H,m), 3.60-3.75(1H,m), 3 3.90-4.10(2H,m), 5.15(1H,d,J=12.3 Hz), 5.20(1H,d,J=12.3 Hz), 7.30-7.40(5H,m)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

3.9 - 4.1; 5.15; 5.2; 7.3 - 7.4; 1.34; 2.5 - 2.7; 3.6 - 3.75

Kind of signal

2H,m; 1H,d,J=12.3 Hz; 1H,d,J=12.3 Hz; 5H,m; 3H,d,J=6.6 Hz; 2H,m; 1H,m

Patent; Takeda Pharmaceutical Company Limited; US2009/42967; (2009); (A1) English, View in Reaxys Mass Spectrometry (1)

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Description (Mass Peak Spectrometry)

References

electrospray ionisation (ESI); spectrum

234 m/z

Reaxys ID 10546127 View in Reaxys

6/204 Linear Structure Formula: C13H13NO4 Molecular Formula: C13H13NO4 Molecular Weight: 247.251 Type of Substance: heterocyclic InChI Key: MBYLTDVXLTZTFH-VIFPVBQESA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

1.057

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Reaxys ID 23271787 View in Reaxys

7/204 Linear Structure Formula: C13H13NO4 Molecular Formula: C13H13NO4 Molecular Weight: 247.251 InChI Key: FACMUORAMROMAI-NSHDSACASA-N Note:

O O

N O

Druglikeness (1) 1 of 1

LogP

1.48

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Reaxys ID 19197236 View in Reaxys

8/204

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CAS Registry Number: 1152110-90-1 Chemical Name: phenylmethyl 3,3-dimethyl-4-oxo-1-pyrrolidinecarboxylate Linear Structure Formula: C14H17NO3 Molecular Formula: C14H17NO3 Molecular Weight: 247.294 InChI Key: NSXMOCLPUSHETI-UHFFFAOYSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

1.494

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colorless

Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); (A1) English, View in Reaxys

Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

Molecular peak

References Patent; SMITHKLINE BEECHAM CORPORATION; WO2009/61879; (2009); (A1) English, View in Reaxys

Reaxys ID 1469385 View in Reaxys

9/204 CAS Registry Number: 16217-19-9 Chemical Name: N-Benzyloxycarbonyl-4-oxo-L-prolinol Linear Structure Formula: C13H15NO4 Molecular Formula: C13H15NO4 Molecular Weight: 249.266 Type of Substance: heterocyclic InChI Key: AQIRVPDXJAFMDZ-NSHDSACASA-N Note:

O N

HO O

Substance Label (1) Label References XXXIV

Andreatta et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 1493,1506, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.328

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

66.84

Lipinski Number

Veber Number

Further Information (1)

17/232

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Description (Further Information)

References

Further information

Andreatta et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 1493,1506, View in Reaxys

Reaxys ID 9396291 View in Reaxys

10/204 Linear Structure Formula: C12H13NO3S Molecular Formula: C12H13NO3S Molecular Weight: 251.306 Type of Substance: heterocyclic InChI Key: KNAMCTRCRYGFGY-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References 20a

Radics, Gabor; Pires, Raul; Koksch, Beate; El-Kousy, Salah M.; Burger, Klaus; Tetrahedron Letters; vol. 44; nb. 5; (2003); p. 1059 - 1062, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.765

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

85.41

Lipinski Number

Veber Number

Reaxys ID 9702094 View in Reaxys

11/204 Chemical Name: benzyl 3-chloro-2-oxopyrrolidine-1-carboxylate Linear Structure Formula: C12H12ClNO3 Molecular Formula: C12H12ClNO3 Molecular Weight: 253.685 Type of Substance: heterocyclic InChI Key: ZNAZBTLFSQVBPU-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References 8

Barrett, Roger; Caine, Darren M.; Cardwell, Kevin S.; Cooke, Jason W.B.; Lawrence, Ron M.; Scott, Peter; Sjolin, Asa; Tetrahedron Asymmetry; vol. 14; nb. 22; (2003); p. 3627 - 3631, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.858

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

18/232

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NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Barrett, Roger; Caine, Darren M.; Cardwell, Kevin S.; Cooke, Jason W.B.; Lawrence, Ron M.; Scott, Peter; Sjolin, Asa; Tetrahedron Asymmetry; vol. 14; nb. 22; (2003); p. 3627 - 3631, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Barrett, Roger; Caine, Darren M.; Cardwell, Kevin S.; Cooke, Jason W.B.; Lawrence, Ron M.; Scott, Peter; Sjolin, Asa; Tetrahedron Asymmetry; vol. 14; nb. 22; (2003); p. 3627 - 3631, View in Reaxys

Reaxys ID 9772278 View in Reaxys

12/204 CAS Registry Number: 776316-72-4 Linear Structure Formula: C15H17O3N Molecular Formula: C15H17NO3 Molecular Weight: 259.305 Type of Substance: heterocyclic InChI Key: GEFPQKWRTGQTDE-UHFFFAOYSA-N Note:

O N

Substance Label (2) Label References 14

Chavan, Subhash P.; Pathak, Ashok B.; Kalkote, Uttam R.; Synlett; nb. 17; (2007); p. 2635 - 2638, View in Reaxys

19/232

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Chavan, Subhash P.; Pasupathy; Venkatraman; Kale, Ramesh R.; Tetrahedron Letters; vol. 45; nb. 37; (2004); p. 6879 - 6882, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.087

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Reaxys ID 30224342 View in Reaxys

13/204 Linear Structure Formula: C15H19NO3 Molecular Formula: C15H19NO3 Molecular Weight: 261.321 InChI Key: DWXJVOAHFRGKEW-UHFFFAOYSA-N Note:

O N O

Substance Label (1) Label References 26

Tice, Colin M.; Noto, Paul B.; Fan, Kristi Yi; Zhao, Wei; Lotesta, Stephen D.; Dong, Chengguo; Marcus, Andrew P.; Zheng, Ya-Jun; Chen, Guozhou; Wu, Zhongren; Van Orden, Rebecca; Zhou, Jing; Bukhtiyarov, Yuri; Zhao, Yi; Lipinski, Kerri; Howard, Lamont; Guo, Joan; Kandpal, Geeta; Meng, Shi; Hardy, Andrew; Krosky, Paula; Gregg, Richard E.; Leftheris, Katerina; McKeever, Brian M.; Singh, Suresh B.; Lala, Deepak; McGeehan, Gerard M.; Zhuang, Linghang; Claremon, David A.; Bioorganic and Medicinal Chemistry Letters; vol. 26; nb. 20; (2016); p. 5044 - 5050, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.115

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Reaxys ID 89237 View in Reaxys

14/204 CAS Registry Number: 147226-04-8 Chemical Name: (R)-1-((benzyloxy)carbonyl)-4-oxopyrrolidine-2-carboxylic acid; (R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; 1-benzyloxycarbonyl-4-oxo-D-proline; 1Benzyloxycarbonyl-4-oxo-D-prolin Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: RPLLCMZOIFOBIF-LLVKDONJSA-N Note:

O N HO O

Substance Label (2) Label References

20/232

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Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

sc2

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.485

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

99 - 100

Solvent (Melting Point)

diethyl ether; petroleum ether

Patchett; Witkop; Journal of the American Chemical Society; vol. 79; (1957); p. 185,190, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

References Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.07 g/100ml

Solvent (Optical Rotatory Power)

dimethyl sulfoxide

Optical Rotatory Power [deg]

-4.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=1

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-19.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patchett; Witkop; Journal of the American Chemical Society; vol. 79; (1957); p. 185,190, View in Reaxys

21/232

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NMR Spectroscopy (7) 1 of 7

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 7

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 3 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 4 of 7

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

76.85

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 5 of 7

Nucleus (NMR Spectroscopy)

22/232

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Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 6 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

75.4

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 7 of 7

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

350

Frequency (NMR Spectroscopy) [MHz]

75.4

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

References Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

Reaxys ID 89238 View in Reaxys

15/204

23/232

2017-11-12 20:29:58

CAS Registry Number: 64187-47-9 Chemical Name: 1-benzyloxycarbonyl-4-keto-L-proline; (S)-4oxo-1-(benzyloxycarbonyl)pyrrolidine-2-carboxylic acid; (S)-1((benzyloxy)carbonyl)-4-oxopyrrolidine-2-carboxylic acid; (2S)-1-benzyloxycarbonyl-4-oxo-pyrrolidine-2-carboxylic acid; (2S)-4-oxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester; N<(phenylmethoxy)carbonyl>-4-oxo-(S)-proline; 4-oxo-1-<(phenylmethoxy)carbonyl>-L-proline Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: RPLLCMZOIFOBIF-NSHDSACASA-N Note:

O N HO O

Substance Label (9) Label References 3

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

Perez, Heidi L.; Chaudhry, Charu; Emanuel, Stuart L.; Fanslau, Caroline; Fargnoli, Joseph; Gan, Jinping; Kim, Kyoung S.; Lei, Ming; Naglich, Joseph G.; Traeger, Sarah C.; Vuppugalla, Ragini; Wei, Donna D.; Vite, Gregory D.; Talbott, Randy L.; Borzilleri, Robert M.; Journal of Medicinal Chemistry; vol. 58; nb. 3; (2015); p. 1556 - 1562, View in Reaxys

Sanner, Mark A.; Weigelt, Carolyn; Stansberry, Mary; Killeen, Kelly; Michne, William F.; et al.; Journal of Organic Chemistry; vol. 57; nb. 19; (1992); p. 5264 - 5268, View in Reaxys; Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys

Liu, Yi-Tsung; Wong, Jesse K.; Tao, Meng; Osterman, Rebecca; Sannigrahi, Mousumi; Girijavallabhan, Viyyoor M.; Saksena, Anil; Tetrahedron Letters; vol. 45; nb. 32; (2004); p. 6097 - 6100, View in Reaxys

Smith, Elizabeth M.; Swiss, Gerald F.; Neustadt, Bernard R.; McNamara, Paul; Gold, Elijah H.; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 7; (1989); p. 1600 - 1606, View in Reaxys; Patent; Schafmeister, Christian E.; US2004/77879; (2004); (A1) English, View in Reaxys

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys

Yelin; Onoprienko; Russian Journal of Bioorganic Chemistry; vol. 24; nb. 9; (1998); p. 594 - 598, View in Reaxys

6aa

Krapcho; Turk; Cushman; Powell; DeForrest; Spitzmiller; Karanewsky; Duggan; Rovnvak; Schwartz; Natarajan; Godfrey; Ryono; Neubeck; Atwa; Petrillo Jr.; Journal of Medicinal Chemistry; vol. 31; nb. 6; (1988); p. 1148 - 1160, View in Reaxys

Smith, Elisabeth M.; Swiss, Gerald F.; Neustadt, Bernard R.; Gold, Elijah H.; Sommer, Jane A.; et al.; Journal of Medicinal Chemistry; vol. 31; nb. 4; (1988); p. 875 - 885, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.485

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

101 - 102

Solvent (Melting Point)

diethyl ether; petroleum ether

Patchett; Witkop; Journal of the American Chemical Society; vol. 79; (1957); p. 185,190, View in Reaxys Crystal Property Description (2) Colour & Other Location Properties

References

24/232

2017-11-12 20:29:58

yellow

supporting information

yellow

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.19 g/100ml

Solvent (Optical Rotatory Power)

dimethyl sulfoxide

Optical Rotatory Power [deg]

10.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

c=1

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

18.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patchett; Witkop; Journal of the American Chemical Society; vol. 79; (1957); p. 185,190, View in Reaxys NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 5

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

25/232

2017-11-12 20:29:58

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 3 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys 4 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys 5 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

75.4

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys Mass Spectrometry (2)

26/232

2017-11-12 20:29:58

Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

spectrum; electron impact (EI)

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys

Reaxys ID 419902 View in Reaxys

16/204 CAS Registry Number: 80953-62-4; 72580-06-4 Chemical Name: N-(benzyloxycarbonyl)-2-pyrrolidone-2-carboxylic acid; N-benzyloxycarbonyl-pyroglutamic acid; 1-benzyl hydrogen 5-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: VHSFUGXCSGOKJX-UHFFFAOYSA-N Note:

O N

Substance Label (4) Label References 13

Iwata; Arisawa; Hamada; Kita; Mizutani; Tomioka; Itai; Miyamoto; Journal of Medicinal Chemistry; vol. 44; nb. 11; (2001); p. 1718 - 1728, View in Reaxys

Nishitani; Horikawa; Iwasaki; et al.; Journal of Organic Chemistry; vol. 47; nb. 9; (1982); p. 1706 - 1712, View in Reaxys

Kosugi, Yoshiyuki; Hamaguchi, Humiko; Nagasaka, Tatsuo; Ozawa, Naganori; Ohki, Sadao; Heterocycles; vol. 14; nb. 9; (1980); p. 1245 - 1249, View in Reaxys

Z-Pyr-OH; ohne Nr.im Original

Voelter,W. et al.; Monatshefte fuer Chemie; vol. 105; (1974); p. 1110 - 1135, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.066

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

131 - 133

Voelter,W. et al.; Monatshefte fuer Chemie; vol. 105; (1974); p. 1110 - 1135, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-28.7

Wavelength (Optical Ro- 589 tatory Power) [nm]

27/232

2017-11-12 20:29:58

Temperature (Optical Rotatory Power) [°C]

Voelter,W. et al.; Monatshefte fuer Chemie; vol. 105; (1974); p. 1110 - 1135, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- NMR troscopy) Comment (NMR Spectroscopy)

13C-NMR

Voelter,W. et al.; Monatshefte fuer Chemie; vol. 105; (1974); p. 1110 - 1135, View in Reaxys Medchem (3) 1 of 3

Target Name

Alcohol dehydrogenase [NADP(+)] [taurine cattle]

Target Synonyms

akr1a1; alcohol dehydrogenase; aldehyde reductase (alcohol dehydrogenase; aldo-keto reductase family 1 member a1

Target Uniprot ID

q3zcj2

Target, Subunit, Species Alcohol dehydrogenase [NADP(+)] [taurine cattle] Target Mutant/Chimera Details

Alcohol dehydrogenase [NADP(+)] [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition of bovine aldose reductase using D,L-glyceraldehyde (1.5 mM) as a substrate with compound concentration of 15 ug/mL dissolved in DMSO upon incubation in 60 mM sodium phosphate, pH 6.2 for 30 min at 25 degree C was measured by decrease in the oxidation ratio of NADPH in experiment 1

Biological Species/NCBI taurine cattle ID Substance RN

419902View in Reaxys

Substance Dose

15 µg/mL

Measurement Parameter

% Inhibition

Unit

Measurement Object

Decrease in the oxidation ratio of NADPH

Qualitative value

Quantitative value

Measurement pX

4.24

Concomitants: Compound name

D; L-glyceraldehyde

Concomitants: Compound role

SUB; SUB

Iwata; Arisawa; Hamada; Kita; Mizutani; Tomioka; Itai; Miyamoto; Journal of Medicinal Chemistry; vol. 44; nb. 11; (2001); p. 1718 - 1728, View in Reaxys 2 of 3

Target Name

Alcohol dehydrogenase [NADP(+)] [taurine cattle]

Target Synonyms

akr1a1; alcohol dehydrogenase; aldehyde reductase (alcohol dehydrogenase; aldo-keto reductase family 1 member a1

Target Uniprot ID

q3zcj2

Target, Subunit, Species Alcohol dehydrogenase [NADP(+)] [taurine cattle] Target Mutant/Chimera Details

Alcohol dehydrogenase [NADP(+)] [taurine cattle]:Wild

28/232

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Target Species (Bioactivity)

taurine cattle

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition of bovine aldose reductase using D,L-glyceraldehyde (1.5 mM) as a substrate with compound concentration of 15 ug/mL dissolved in DMSO upon incubation uisng 60 mM sodium phosphate, pH 6.2 for 30 min at 25 degree C was measured by decrease in the oxidation ratio of NADPH in experiment 2

Biological Species/NCBI taurine cattle ID Substance RN

419902View in Reaxys

Substance Dose

15 µg/mL

Measurement Parameter

% Inhibition

Unit

Measurement Object

Oxidation of NADPH

Qualitative value

Quantitative value

Measurement pX

4.19

Concomitants: Compound name

D; L-glyceraldehyde

Concomitants: Compound role

SUB; SUB

Iwata; Arisawa; Hamada; Kita; Mizutani; Tomioka; Itai; Miyamoto; Journal of Medicinal Chemistry; vol. 44; nb. 11; (2001); p. 1718 - 1728, View in Reaxys 3 of 3

Target Name

Alcohol dehydrogenase [NADP(+)] [taurine cattle]

Target Synonyms

akr1a1; alcohol dehydrogenase; aldehyde reductase (alcohol dehydrogenase; aldo-keto reductase family 1 member a1

Target Uniprot ID

q3zcj2

Target, Subunit, Species Alcohol dehydrogenase [NADP(+)] [taurine cattle] Target Mutant/Chimera Details

Alcohol dehydrogenase [NADP(+)] [taurine cattle]:Wild

Target Species (Bioactivity)

taurine cattle

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibition of bovine aldose reductase using D,L-glyceraldehyde (1.5 mM) as a substrate with compound concentration of 5 ug/mL dissolved in DMSO upon incubation in 60 mM sodium phosphate, pH 6.2 for 30 min at 25 degree C was measured by decrease in the oxidation ratio of NADPH

Biological Species/NCBI taurine cattle ID Substance RN

419902View in Reaxys

Measurement Parameter

% Inhibition

Unit

Measurement Object

Decrease in the oxidation ratio of NADPH

Qualitative value

Quantitative value

29/232

2017-11-12 20:29:58

Concomitants: Compound name

D; L-glyceraldehyde

Concomitants: Compound role

SUB; SUB

Iwata; Arisawa; Hamada; Kita; Mizutani; Tomioka; Itai; Miyamoto; Journal of Medicinal Chemistry; vol. 44; nb. 11; (2001); p. 1718 - 1728, View in Reaxys

Reaxys ID 486712 View in Reaxys

17/204 CAS Registry Number: 105903-44-4 Chemical Name: 4-oxo-1-(benzyloxycarbonyl)pyrrolidine-(S)-2carboxylic acid; 4-keto-1[(phenylmethoxy)carbonyl]-L-proline; 1benzyloxycarbonyl-4-oxoproline; Benzyloxycarbonyl-4-oxo-prolin Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: RPLLCMZOIFOBIF-UHFFFAOYSA-N Note:

O N HO O

Druglikeness (1) 1 of 1

LogP

0.485

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

95 - 97

Wieland,T. et al.; Justus Liebigs Annalen der Chemie; (1977); p. 806 - 810, View in Reaxys

Reaxys ID 3556609 View in Reaxys

O O HO

18/204 CAS Registry Number: 32159-21-0 Chemical Name: Cbz-L-pGlu-OH; Z-Pyr-OH Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: VHSFUGXCSGOKJX-JTQLQIEISA-N Note:

O N

Substance Label (18) Label References 11

Miyazaki, Masaki; Naito, Hiroyuki; Sugimoto, Yuuichi; Yoshida, Keisuke; Kawato, Haruko; Okayama, Tooru; Shimizu, Hironari; Miyazaki, Masaya; Kitagawa, Mayumi; Seki, Takahiko; Fukutake, Setsuko; Shiose, Yoshinobu; Aonuma, Masashi; Soga, Tsunehiko; Bioorganic and Medicinal Chemistry; vol. 21; nb. 14; (2013); p. 4319 - 4331, View in Reaxys

Katritzky, Alan R.; Angrish, Parul; Todadze, Ekaterina; Ghiviriga, Ion; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 21; (2007); p. 6000 - 6002, View in Reaxys

30/232

2017-11-12 20:29:58

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys; Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys

(Z)-pGlu

Prokai, Laszlo; Prokai-Tatrai, Katalin; Zharikova, Alevtina D.; Nguyen, Vien; Perjesi, Pal; Stevens Jr., Stanley M.; Journal of Medicinal Chemistry; vol. 47; nb. 24; (2004); p. 6025 - 6033, View in Reaxys

Edwards, Christopher W.; Shipton, Mark R.; Alcock, Nathaniel W.; Clase, Howard; Wills, Martin; Tetrahedron; vol. 59; nb. 34; (2003); p. 6473 - 6480, View in Reaxys

Kigoshi, Hideo; Hayashi, Norimitsu; Uemura, Daisuke; Tetrahedron Letters; vol. 42; nb. 42; (2001); p. 7469 - 7471, View in Reaxys

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys

7 (R1=PhCH2)

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys

Melnyk, Patricia; Ducrot, Pierre; Demuynck, Luc; Thal, Claude; Tetrahedron Letters; vol. 34; nb. 32; (1993); p. 5085 - 5088, View in Reaxys

Altmann, Karl-Heinz; Tetrahedron Letters; vol. 34; nb. 48; (1993); p. 7721 - 7724, View in Reaxys

Bousquet; De Regis; Giannola; Santagati; Tirendi; Pharmazie; vol. 48; nb. 4; (1993); p. 260 - 262, View in Reaxys

Shiozaki; Synthesis; nb. 8; (1990); p. 691 - 693, View in Reaxys

L-5

Sisto; Verdini; Virdia; Synthesis; vol. NO. 3; (1985); p. 294 - 296, View in Reaxys

Chorev; Rubini; Gilon; Wormser; Selinger; Journal of Medicinal Chemistry; vol. 26; nb. 2; (1983); p. 129 135, View in Reaxys

Fig. 1

Abiko; Sekino; Chemical and Pharmaceutical Bulletin; vol. 30; nb. 12; (1982); p. 4448 - 4456, View in Reaxys

Shvachkin, Yu. P.; Smirnova, A. P.; Fedotov, V. P.; Bushueva, G. I.; J. Gen. Chem. USSR (Engl. Transl.); vol. 52; nb. 5; (1982); p. 1202 - 1206,1054 - 1057, View in Reaxys

Cavrini; Chiarini; Garuti; Giovanninetti; Il Farmaco; edizione scientifica; vol. 31; nb. 8; (1976); p. 599 606, View in Reaxys

IVa

Gibian,H.; Klieger,E.; Justus Liebigs Annalen der Chemie; vol. 640; (1961); p. 145 - 156, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.066

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Melting Point (4) 1 of 4

Melting Point [°C]

134 - 135

Solvent (Melting Point)

ethyl acetate

Bousquet; De Regis; Giannola; Santagati; Tirendi; Pharmazie; vol. 48; nb. 4; (1993); p. 260 - 262, View in Reaxys 2 of 4

Melting Point [°C]

128.5 - 130

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 3 of 4

Melting Point [°C]

135 - 136

31/232

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Imaki, Katsuhiro; Niwa, Haruki; Sakuyama, Shigeru; Okada, Takanori; Toda, Masaaki; Hayashi, Masaki; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 9; (1981); p. 2699 - 2701, View in Reaxys 4 of 4

Melting Point [°C]

134 - 135

Solvent (Melting Point)

ethyl acetate; petroleum ether

Gibian,H.; Klieger,E.; Justus Liebigs Annalen der Chemie; vol. 640; (1961); p. 145 - 156, View in Reaxys Optical Rotatory Power (4) 1 of 4

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.47 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-23.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys 2 of 4

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.75 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-20

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 3 of 4

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.00 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-29.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Imaki, Katsuhiro; Niwa, Haruki; Sakuyama, Shigeru; Okada, Takanori; Toda, Masaaki; Hayashi, Masaki; Chemical & Pharmaceutical Bulletin; vol. 29; nb. 9; (1981); p. 2699 - 2701, View in Reaxys 4 of 4

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

32/232

2017-11-12 20:29:58

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-29.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Gibian,H.; Klieger,E.; Justus Liebigs Annalen der Chemie; vol. 640; (1961); p. 145 - 156, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys; Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 2 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys; Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

15N

Solvents (NMR Spectro- dimethylsulfoxide scopy) Temperature (NMR Spectroscopy) [°C]

28 - 30

Kricheldorf, Hans R.; Organic Magnetic Resonance; vol. 15; nb. 2; (1981); p. 162 - 177, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1790 - 1730 cm**(-1)

33/232

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Bousquet; De Regis; Giannola; Santagati; Tirendi; Pharmazie; vol. 48; nb. 4; (1993); p. 260 - 262, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3440 - 1720 cm**(-1)

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys Mass Spectrometry (1) Comment (Mass References Spectrometry) Molecular peak

Patent; Rinehart; Kenneth L.; Sanborn; Alexandra J.; Wilson; George R.; US6034058; (2000); (A1) English, View in Reaxys

Reaxys ID 4698210 View in Reaxys

19/204 CAS Registry Number: 78339-57-8 Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: VHSFUGXCSGOKJX-SNVBAGLBSA-N Note:

O N

Substance Label (1) Label References (D-5)

Sisto; Verdini; Virdia; Synthesis; vol. NO. 3; (1985); p. 294 - 296, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.066

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 4698211 View in Reaxys

20/204 CAS Registry Number: 32159-21-0 Chemical Name: 1-benzyl hydrogen (S)-5-oxopyrrolidine-1,2dicarboxylate; N-benzyloxycarbonyl-pyroglutamic acid Linear Structure Formula: C13H13NO5 Molecular Formula: C13H13NO5 Molecular Weight: 263.25 Type of Substance: heterocyclic InChI Key: VHSFUGXCSGOKJX-UHFFFAOYSA-N Note:

O N

HO L-isomer

Substance Label (1) Label References

34/232

2017-11-12 20:29:58

N-Z-pGlu

Grim, Michael D.; Chauhan, Virander; Shimohigashi, Yasuyuki; Kolar, Aldean J.; Stammer, Charles H.; Journal of Organic Chemistry; vol. 46; nb. 13; (1981); p. 2671 - 2673, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.066

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 7489185 View in Reaxys

21/204 Chemical Name: N-(benzyloxycarbonyl)-<3-(2)H>pyroglutamic acid; N-(benzyloxycarbonyl)-(3-(2)H)pyroglutamic acid Linear Structure Formula: C13H12DNO5 Molecular Formula: C13H13NO5 Molecular Weight: 264.242 Type of Substance: heterocyclic InChI Key: VHSFUGXCSGOKJX-UKQOPZMLSA-N Note:

O N

HO 2

Substance Label (1) Label References 7 (R1=PhCH2, H %B&=(2)H)

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.066

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 7490585 View in Reaxys

O O HO

22/204 Chemical Name: N-(benzyloxycarbonyl)-<2,3-(2)H2>pyroglutamic acid; N-(benzyloxycarbonyl)-(2,3-(2)H2)pyroglutamic acid Linear Structure Formula: C13H11D2NO5 Molecular Formula: C13H13NO5 Molecular Weight: 265.234 Type of Substance: heterocyclic InChI Key: VHSFUGXCSGOKJX-JOJMAIMDSA-N Note:

O N

H 2H

Substance Label (1) Label References 7 (H%A&=2H=(2)H)

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys

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Druglikeness (1) 1 of 1

LogP

1.066

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 21706429 View in Reaxys

23/204 CAS Registry Number: 1266145-47-4 Linear Structure Formula: C16H19NO3 Molecular Formula: C16H19NO3 Molecular Weight: 273.332 InChI Key: OPZCACNJWHAFNQ-AWEZNQCLSA-N Note:

N O O

Druglikeness (1) 1 of 1

LogP

2.127

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Reaxys ID 21706430 View in Reaxys

24/204 Linear Structure Formula: C16H19NO3 Molecular Formula: C16H19NO3 Molecular Weight: 273.332 InChI Key: OPZCACNJWHAFNQ-CQSZACIVSA-N Note:

N O O

Druglikeness (1) 1 of 1

LogP

2.127

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

36/232

2017-11-12 20:29:58

Reaxys ID 30187025 View in Reaxys

25/204 Chemical Name: 1-benzyloxycarbonyl-2-methoxycarbonyl-4oxopyrrole Linear Structure Formula: C14H13NO5 Molecular Formula: C14H13NO5 Molecular Weight: 275.261 InChI Key: XMPQEXPXBQVDMN-UHFFFAOYSA-N Note:

O N

O O O

Druglikeness (1) 1 of 1

LogP

1.231

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 491533 View in Reaxys

26/204 CAS Registry Number: 16217-15-5; 132431-11-9 Chemical Name: 1-benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate; (S)-1-benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate; 1-benzyl-2-methyl 4-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: XRFKZAWVKVORNI-UHFFFAOYSA-N Note:

O N O O

Substance Label (1) Label References entry 4 (subs.)

Subhas Bose; Thurston, David E.; Tetrahedron Letters; vol. 31; nb. 47; (1990); p. 6903 - 6906, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.806

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

2.58 - 2.63; 2.9 - 2.99; 3.62; 3.77; 3.95 - 4.02; 4.82 - 4.89; 5.11 - 5.24; 7.32 - 7.39

Kind of signal

m, 1H; m, 1H; s, 3H, rotamers; m, 2H; m, 1H; m, 2H; m, 5H

NMR (CDCl3) δ 2.58-2.63 (m, 1H), 2.90-2.99 (m, 1H), 3.62, 3.77 (s, 3H, rotamers), 3.95-4.02 (m, 2H), 4.82-4.89 (m, 1H), 5.11-5.24 (m, 2H), 7.32-7.39 (m, 5H)

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Patent; Bristol-Myers Squibb Company; US2009/274648; (2009); (A1) English, View in Reaxys

Reaxys ID 491534 View in Reaxys

O O O

27/204 CAS Registry Number: 16217-15-5 Chemical Name: 1-benzyloxycarbonyl-4-oxo-L-proline methyl ester; 1-benzyloxycarbonyl-4-keto-(S)-proline methyl ester; N<(phenylmethoxy)carbonyl>-4-oxo-(S)-proline methyl ester; methyl (2S)-1-(benzyloxycarbonyl)-4-oxo-2-pyrrolidinecarboxylate; 4-oxo-1-<(phenylmethoxy)carbonyl>-L-proline methyl ester; methyl (2S)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate; methyl (2S)-N-benzyloxycarbonyl-4-oxopyrrolidine-2carboxylate Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: XRFKZAWVKVORNI-LBPRGKRZSA-N Note:

O N

H O

Substance Label (14) Label References 10

Wang, Alan Xiangdong; Chen, Jie; Zhao, Qian; Sun, Li-Qiang; Friborg, Jacques; Yu, Fei; Hernandez, Dennis; Good, Andrew C.; Klei, Herbert E.; Rajamani, Ramkumar; Mosure, Kathy; Knipe, Jay O.; Li, Danshi; Zhu, Jialong; Levesque, Paul C.; McPhee, Fiona; Meanwell, Nicholas A.; Scola, Paul M.; Bioorganic and Medicinal Chemistry Letters; vol. 27; nb. 3; (2017); p. 590 - 596, View in Reaxys

Q-4

Patent; Sunshine Lake Pharma Co., Ltd; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2014); (A1) English, View in Reaxys; Patent; Sunshine Lake Pharma Co., Ltd.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2015); (B1) English, View in Reaxys

20-4

Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; LI, Shifeng; FU, Changping; HU, Bailin; WU, Xiwei; TANG, Changhua; WO2014/82380; (2014); (A1) English, View in Reaxys

19-5

Patent; SUNSHINE LAKE PHARMA CO., LTD.; ZHANG, Yingjun; ZHANG, Jiancun; XIE, Hongming; REN, Qingyun; HU, Bailin; LI, Shifeng; WU, Xiwei; TANG, Changhua; WANG, Chenglin; FANG, Qinghong; YU, Quanxing; ZHANG, Zhikeng; WO2014/131315; (2014); (A1) English, View in Reaxys

(2S)-13e

Zhao, Xueqing; Pabel, Joerg; Hoefner, Georg C.; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 2; (2013); p. 470 - 484, View in Reaxys

intermediate 23

Patent; GLAXOSMITHKLINE LLC; CHEN, Pingyun; COUCH, Ricky; DUAN, Maosheng; GRIMES, Richard, Martin; KAZMIERSKI, Wieslaw, Mieczyslaw; NORTON, Beth, Adams; TALLANT, Matthew; WO2011/28596; (2011); (A1) English, View in Reaxys

Kondo, Takashi; Nekado, Takahiro; Sugimoto, Isamu; Ochi, Kenya; Takai, Shigeyuki; Kinoshita, Atsushi; Tajima, Yohei; Yamamoto, Susumu; Kawabata, Kazuhito; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 15; nb. 7; (2007); p. 2631 - 2650, View in Reaxys

Gardelli, Cristina; Nizi, Emanuela; Muraglia, Ester; Crescenzi, Benedetta; Ferrara, Marco; Orvieto, Federica; Pace, Paola; Pescatore, Giovanna; Poma, Marco; Ferreira, Maria Del Rosario Rico; Scarpelli, Rita; Homnick, Carl F.; Ikemoto, Norihiro; Alfieri, Anna; Verdirame, Maria; Bonelli, Fabio; Paz, Odalys Gonzalez; Taliani, Marina; Monteagudo, Edith; Pesci, Silvia; Laufer, Ralph; Felock, Peter; Stillmock, Kara A.; Hazuda, Daria; Rowley, Michael; Summa, Vincenzo; Journal of Medicinal Chemistry; vol. 50; nb. 20; (2007); p. 4953 - 4975, View in Reaxys

23.02

Patent; SCHERING CORPORATION; WO2005/85242; (2005); (A1) English, View in Reaxys; Patent; SCHERING CORPORATION; WO2005/87725; (2005); (A2) English, View in Reaxys; Patent; SCHERING CORPORATION; WO2005/85197; (2005); (A1) English, View in Reaxys; Patent; SCHERING CORPORATION; WO2005/87721; (2005); (A2) English, View in Reaxys

Kemp, D.S.; Carter, Jeffery S.; Journal of Organic Chemistry; vol. 54; nb. 1; (1989); p. 109 - 115, View in Reaxys

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Smith, Elisabeth M.; Swiss, Gerald F.; Neustadt, Bernard R.; Gold, Elijah H.; Sommer, Jane A.; et al.; Journal of Medicinal Chemistry; vol. 31; nb. 4; (1988); p. 875 - 885, View in Reaxys

Chowdhury,A.K.A. et al.; Journal of Medicinal Chemistry; vol. 21; (1978); p. 607 - 612, View in Reaxys

Ketoester XXXIII

Andreatta et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 1493,1506, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.806

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (6) Colour & Other Location Properties

References

yellow

Paragraph 0708

yellow

Paragraph 00513

yellow

Page/Page column 176

colourless

Zhao, Xueqing; Pabel, Joerg; Hoefner, Georg C.; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 2; (2013); p. 470 - 484, View in Reaxys

light-brown

Page/Page column 10

light-brown

Patent; Bristol-Myers Squibb Company; US2010/150866; (2010); (A1) English, View in Reaxys Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64061; (2008); (A1) English, View in Reaxys; Patent; Bristol-Myers Squibb Company; US2009/297472; (2009); (A1) English, View in Reaxys

Further Information (1) Description (Fur- References ther Information) Further information

Andreatta et al.; Australian Journal of Chemistry; vol. 20; (1967); p. 1493,1506, View in Reaxys

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.1 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

17.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Zhao, Xueqing; Pabel, Joerg; Hoefner, Georg C.; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 2; (2013); p. 470 - 484, View in Reaxys

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2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.3 g/100ml

Solvent (Optical Rotatory Power)

dioxane

Optical Rotatory Power [deg]

5.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Smith, Elisabeth M.; Swiss, Gerald F.; Neustadt, Bernard R.; Gold, Elijah H.; Sommer, Jane A.; et al.; Journal of Medicinal Chemistry; vol. 31; nb. 4; (1988); p. 875 - 885, View in Reaxys NMR Spectroscopy (13) 1 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

Paragraph 0708

NMR (400 MHz, CD3Cl): δ 7.47 (d, J = 8.24 Hz, 2H), 7.38 (d, J = 8.24 Hz, 2H), 7.24 (m, 1H), 5.09 (s, 2H), 4.18(t, 1H), 3.68 (s, 3H), 3.38 (m, 1H), 3.32 (m, 1H), 2.21 (m, 1H), 1.96 (m, 1H).

Patent; Sunshine Lake Pharma Co., Ltd.; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2015); (B1) English, View in Reaxys 2 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 Hz, CDC1 ) δ (ppm): 7.47 (d, 2H, J = 8.24 Hz), 7.38 (d, 2H, J = 8.24 Hz), 3 7.24 (m, 1H), 5.09 (s, 2H), 4.18 (t, 1H), 3.68 (s, 3H), 3.38 (m, 1H), 3.32 (m, 1H), 2.21 (m, 1H), 1.96 (m, 1H).

Location

Paragraph 00513

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

Paragraph 0708

NMR (400 MHz, CD3Cl): δ 7.47 (d, J = 8.24 Hz, 2H), 7.38 (d, J = 8.24 Hz, 2H), 7.24 (m, 1H), 5.09 (s, 2H), 4.18 (t, 1H), 3.68 (s, 3H), 3.38 (m, 1H), 3.32 (m, 1H), 2.21 (m, 1H), 1.96 (m, 1H).

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Patent; Sunshine Lake Pharma Co., Ltd; ZHANG, Jiancun; ZHANG, Yingjun; XIE, Hongming; REN, Qingyun; LUO, Huichao; YU, Tianzhu; TAN, Yumei; EP2730572; (2014); (A1) English, View in Reaxys 4 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 Hz, CDCI3): δ 7.47 (d, 2H, J = 8.24 Hz), 7.38 (d, 2H, J = 8.24 Hz), 7.24 (m, 1H), 5.09 (s, 2H), 4.18 (t, 1H), 3.68 (s, 3H), 3.38 (m, 1H), 3.32 (m, 1H), 2.21 (m, 1H), 1.96 (m, 1H) ppm.

Location

Page/Page column 176

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

Page/Page column 26

Comment (NMR Spectroscopy)

Signals given

NMR (400 MHz, CHLOROFORM-c/) δ ppm 7.29 - 7.56 (m, 5 H) 5.08 - 5.37 (m, 2 H) 4.80 - 5.02 (m, 1 H) 3.89 - 4.08 (m, 2 H) 3.53 - 3.88 (m, 3 H) 2.95 (dd, J=18.82, 10.79 Hz, 1 H) 2.63 (dd, 1 H).

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H NMR (300 MHz, CDCl3) δ 7.42-7.29 (m, 5H), 5.20-5.09 (m, 2H), 4.94-4.81 (m, 1H), 4.07-3.59 (m, 5H), 3.04-2.87 (m, 1H), 2.67-2.56 (m, 1H)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.29 - 7.42; 5.09 - 5.2; 4.81 - 4.94; 3.59 - 4.07; 2.87 - 3.04; 2.56 - 2.67

Kind of signal

m, 5H; m, 2H; m, 1H; m, 5H; m, 1H; m, 1H

Patent; Vicuron Pharmaceuticals Inc.; US2010/22605; (2010); (A1) English, View in Reaxys 7 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Location

Page/Page column 10

NMR (CDCl3) δ 2.58-2.63 (m, 1H), 2.90-2.99 (m, 1H), 3.62, 3.77 (s, 3H, rotamers), 3.95-4.02 (m, 2H), 4.82-4.89 (m, 1H), 5.11-5.24 (m, 2H), 7.32-7.39 (m, 5H).

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Comment (NMR Spectroscopy)

Signals given

Patent; Bristol-Myers Squibb Company; US2010/150866; (2010); (A1) English, View in Reaxys 8 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3) δ 2.58-2.63 (m, 1H), 2.90-2.99 (m, 1H), 3.62, 3.77 (s, 3H, rotamers), 3.95-4.02 (m, 2H), 4.82-4.89 (m, 1H), 5.11-5.24 (m, 2H), 7.32-7.39 (m, 5H).

Patent; Bristol-Myers Squibb Company; US2009/297472; (2009); (A1) English, View in Reaxys 9 of 13

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3) δ 2.58-2.63 (m, 1 H), 2.90-2.99 (m, 1 H), 3.62, 3.77 (s, 3 H, rotamers), 3.95-4.02 (m, 2 H), 4.82-4.89 (m, 1 H), 5.11-5.24 (m, 2 H), 7.32-7.39 (m, 5 H).

Patent; BRISTOL-MYERS SQUIBB COMPANY; WO2008/64061; (2008); (A1) English, View in Reaxys 10 of 13

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6; trifluoroacetic acid scopy) Temperature (NMR Spectroscopy) [°C]

56.84

Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

42/232

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Ganellin, C. Robin; Bishop, Paul B.; Bambal, Ramesh B.; Chan, Suzanne M. T.; Leblond, Bertrand; Moore, Andrew N. J.; Zhao, Lihua; Bourgeat, Pierre; Rose, Christiane; Vargas, Froylan; Schwartz, Jean-Charles; Journal of Medicinal Chemistry; vol. 48; nb. 23; (2005); p. 7333 - 7342, View in Reaxys 13 of 13

Description (NMR Spec- NMR troscopy) Chowdhury,A.K.A. et al.; Journal of Medicinal Chemistry; vol. 21; (1978); p. 607 - 612, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Chowdhury,A.K.A. et al.; Journal of Medicinal Chemistry; vol. 21; (1978); p. 607 - 612, View in Reaxys

Reaxys ID 3983116 View in Reaxys

28/204 CAS Registry Number: 92249-27-9 Chemical Name: 1-(benzyloxycarbonyl)-2-(methoxycarbonyl)-3-oxopyrrolidine; 1-benzyl-2-methyl-3-oxo-pyrrolidine-1,2-dicarboxylate; N-Benzyloxycrbonyl-3-oxo-DL-prolin-methylester Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: CEFMFNNINXGTQC-UHFFFAOYSA-N Note:

O O N O O

Substance Label (1) Label References 19

Moyer, Mikel P.; Feldman, Paul L.; Rapoport, Henry; Journal of Organic Chemistry; vol. 50; nb. 25; (1985); p. 5223 - 5230, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.568

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Moyer, Mikel P.; Feldman, Paul L.; Rapoport, Henry; Journal of Organic Chemistry; vol. 50; nb. 25; (1985); p. 5223 - 5230, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

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Solvents (NMR Spectro- CDCl3 scopy) Moyer, Mikel P.; Feldman, Paul L.; Rapoport, Henry; Journal of Organic Chemistry; vol. 50; nb. 25; (1985); p. 5223 - 5230, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

2975 - 1700 cm**(-1)

Moyer, Mikel P.; Feldman, Paul L.; Rapoport, Henry; Journal of Organic Chemistry; vol. 50; nb. 25; (1985); p. 5223 - 5230, View in Reaxys

Reaxys ID 4508880 View in Reaxys

29/204 CAS Registry Number: 75857-94-2 Chemical Name: (5S)-N-(benzyloxycarbonyl)-5-methoxycarbonyl-2-pyrrolidinone; N-benzyloxycarbonylpyroglutamate methyl ester; methyl N-benzyloxycarbonyl-L-pyroglutamate; methyl L-1-benzyloxycarbonylpyroglutamate; N-carbamoyl-Lpyroglutamate; (S)-5-oxo-1,2-pyrrolidinedicarboxylic acid 2methyl 1-(phenylmethyl) diester Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: MBOBZGBHABMDMC-NSHDSACASA-N Note:

O N

Substance Label (14) Label References compound A

Patent; Bracco Imaging S.p.A; EP1935435; (2008); (A2) English, View in Reaxys

N-CBz-L-pyroglutam.-OMe

Baran, Phil S.; Hafensteiner, Benjamin D.; Ambhaikar, Narendra B.; Guerrero, Carlos A.; Gallagher, John D.; Journal of the American Chemical Society; vol. 128; nb. 26; (2006); p. 8678 - 8693, View in Reaxys

Szemes Jr., Fridrich; Pousse, Anthony; Othman, Raja Ben; Bousquet, Till; Othman, Mohamed; Dalla, Vincent; Synthesis; nb. 5; (2006); p. 875 - 879, View in Reaxys

Yu, Jurong; Truc, Vu; Riebel, Peter; Hierl, Elizabeth; Mudryk, Boguslaw; Tetrahedron Letters; vol. 46; nb. 23; (2005); p. 4011 - 4013, View in Reaxys

10a

Rudolph, Alexander C.; Machauer, Rainer; Martin, Stephen F.; Tetrahedron Letters; vol. 45; nb. 25; (2004); p. 4895 - 4898, View in Reaxys

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys

Lee, Yong Sup; Cho, Dae Joo; Kim, Sun Nam; Choi, Jung Hoon; Park, Hokoon; Journal of Organic Chemistry; vol. 64; nb. 26; (1999); p. 9727 - 9730, View in Reaxys

Sutherland; Willis; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 38; nb. 1; (1996); p. 95 - 102, View in Reaxys

Adams, David R.; Bailey, Patrick D.; Collier, Ian D.; Heffernan, John D.; Stokes, Stephen; Chemical Communications; nb. 3; (1996); p. 349 - 350, View in Reaxys

Li; Sakamoto; Kato; Kikugawa; Synthetic Communications; vol. 25; nb. 24; (1995); p. 4045 - 4052, View in Reaxys

5 R = PhCH2

Magnus, Philip; Hulme, Christopher; Tetrahedron Letters; vol. 35; nb. 44; (1994); p. 8097 - 8100, View in Reaxys

Ohta, Tomihisa; Shiokawa, Sojiro; Iwashita, Eiichiro; Sato, Nobuaki; Sakurai, Kuniya; et al.; Heterocycles; vol. 33; nb. 1; (1992); p. 143 - 146, View in Reaxys

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Yoshifuji,Shigeyuki; Tanaka, Ken-ichi; Kawai, Tomoyuki; Nitta, Yoshihiro; Chemical & Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3873 - 3878, View in Reaxys

Yoshifuji, Shigeyuki; Matsumoto, Hideyo; Tanaka, Ken-ichi; Nitta, Yoshihiro; Tetrahedron Letters; vol. 21; (1980); p. 2963 - 2964, View in Reaxys

Patent-Specific Data (1) References Patent; Bracco Imaging S.p.A; EP1935435; (2008); (A2) English, View in Reaxys Druglikeness (1) 1 of 1

LogP

1.387

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

71 - 72

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys Crystal Property Description (2) Colour & Other References Properties colourless

Zhou, Dejun; Toyooka, Naoki; Nemoto, Hideo; Yamaguchi, Kaoru; Tsuneki, Hiroshi; Wada, Tsutomu; Sasaoka, Toshiyasu; Sakai, Hideki; Tezuka, Yasuhiro; Kadota, Shigetoshi; Jones, Tappey H.; Garraffo, H. Martin; Spande, Thomas F.; Daly, John W.; Heterocycles; vol. 79; nb. C; (2009); p. 565 - 571, View in Reaxys

light-yellow

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys

Optical Rotatory Power (11) 1 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.95 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-44.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 2 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/l

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-42.97

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2017-11-12 20:29:58

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Bracco Imaging S.p.A; EP1935435; (2008); (A2) English, View in Reaxys 3 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/l

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-44.79

Wavelength (Optical Ro- 578 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Bracco Imaging S.p.A; EP1935435; (2008); (A2) English, View in Reaxys 4 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/l

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-50.09

Wavelength (Optical Ro- 546 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Bracco Imaging S.p.A; EP1935435; (2008); (A2) English, View in Reaxys 5 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/l

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-100.43

Wavelength (Optical Ro- 365 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Bracco Imaging S.p.A; EP1935435; (2008); (A2) English, View in Reaxys 6 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3.5 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-45

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Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys 7 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-41.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Lee, Yong Sup; Cho, Dae Joo; Kim, Sun Nam; Choi, Jung Hoon; Park, Hokoon; Journal of Organic Chemistry; vol. 64; nb. 26; (1999); p. 9727 - 9730, View in Reaxys 8 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-26

Wavelength (Optical Ro- 589 tatory Power) [nm] Sutherland; Willis; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 38; nb. 1; (1996); p. 95 - 102, View in Reaxys 9 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.42 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-45.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Li; Sakamoto; Kato; Kikugawa; Synthetic Communications; vol. 25; nb. 24; (1995); p. 4045 - 4052, View in Reaxys 10 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-43.1

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Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Yoshifuji,Shigeyuki; Tanaka, Ken-ichi; Kawai, Tomoyuki; Nitta, Yoshihiro; Chemical & Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3873 - 3878, View in Reaxys 11 of 11

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-41.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Yoshifuji, Shigeyuki; Matsumoto, Hideyo; Tanaka, Ken-ichi; Nitta, Yoshihiro; Tetrahedron Letters; vol. 21; (1980); p. 2963 - 2964, View in Reaxys NMR Spectroscopy (9) 1 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 2 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 3 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lee, Yong Sup; Cho, Dae Joo; Kim, Sun Nam; Choi, Jung Hoon; Park, Hokoon; Journal of Organic Chemistry; vol. 64; nb. 26; (1999); p. 9727 - 9730, View in Reaxys; Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys

48/232

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4 of 9

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Lee, Yong Sup; Cho, Dae Joo; Kim, Sun Nam; Choi, Jung Hoon; Park, Hokoon; Journal of Organic Chemistry; vol. 64; nb. 26; (1999); p. 9727 - 9730, View in Reaxys 5 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Lee, Yong Sup; Cho, Dae Joo; Kim, Sun Nam; Choi, Jung Hoon; Park, Hokoon; Journal of Organic Chemistry; vol. 64; nb. 26; (1999); p. 9727 - 9730, View in Reaxys 6 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Sutherland; Willis; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 38; nb. 1; (1996); p. 95 - 102, View in Reaxys 7 of 9

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Sutherland; Willis; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 38; nb. 1; (1996); p. 95 - 102, View in Reaxys 8 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

Yoshifuji,Shigeyuki; Tanaka, Ken-ichi; Kawai, Tomoyuki; Nitta, Yoshihiro; Chemical & Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3873 - 3878, View in Reaxys 9 of 9

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

Comment (NMR Spectroscopy)

1H-1H.

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Yoshifuji,Shigeyuki; Tanaka, Ken-ichi; Kawai, Tomoyuki; Nitta, Yoshihiro; Chemical & Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3873 - 3878, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1800 - 1720 cm**(-1)

Yoshifuji,Shigeyuki; Tanaka, Ken-ichi; Kawai, Tomoyuki; Nitta, Yoshihiro; Chemical & Pharmaceutical Bulletin; vol. 34; nb. 9; (1986); p. 3873 - 3878, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) chemical ionization (CI); spectrum

Sutherland; Willis; Journal of Labelled Compounds and Radiopharmaceuticals; vol. 38; nb. 1; (1996); p. 95 - 102, View in Reaxys

Reaxys ID 5085572 View in Reaxys

30/204 CAS Registry Number: 75857-94-2 Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: MBOBZGBHABMDMC-UHFFFAOYSA-N Note:

O N

O L-isomer

Substance Label (1) Label References Table 1, entry f,g

Ohta, Tomihisa; Kimura, Toshihiko; Sato, Nobuaki; Nozoe, Shigeo; Tetrahedron Letters; vol. 29; nb. 34; (1988); p. 4303 - 4304, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.387

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 9337628 View in Reaxys

31/204 Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: DGVPIVMXDYDTID-CABZTGNLSA-N Note:

O N

50/232

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Druglikeness (1) 1 of 1

LogP

1.363

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 9774672 View in Reaxys

32/204 CAS Registry Number: 690211-34-8 Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: MBOBZGBHABMDMC-LLVKDONJSA-N Note:

O N

Substance Label (2) Label References 5

Brenneman, Jehrod B.; Martin, Stephen F.; Organic Letters; vol. 6; nb. 8; (2004); p. 1329 - 1331, View in Reaxys

16c

Brenneman, Jehrod B.; Machauer, Rainer; Martin, Stephen F.; Tetrahedron; vol. 60; nb. 34; (2004); p. 7301 - 7314, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.387

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 10165951 View in Reaxys

33/204 Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 Type of Substance: heterocyclic InChI Key: MBOBZGBHABMDMC-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References 5

Baran, Phil S.; Guerrero, Carlos A.; Ambhaikar, Narendra B.; Hafensteiner, Benjamin D.; Angewandte Chemie - International Edition; vol. 44; nb. 4; (2005); p. 606 - 609, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.387

51/232

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H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 23263666 View in Reaxys

34/204 CAS Registry Number: 132431-11-9 Chemical Name: methyl (2R)-1-benzyloxycarbonyl-4-oxopyrrolidine-2-carboxylate; (R)-1-benzyl 2-methyl 4-oxopyrrolidine-1,2-dicarboxylate; 1-benzyl 2-methyl (R)-4-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C14H15NO5 Molecular Formula: C14H15NO5 Molecular Weight: 277.277 InChI Key: XRFKZAWVKVORNI-GFCCVEGCSA-N Note:

N O O

Substance Label (3) Label References 12A

Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; ELLSWORTH, Bruce A; JURICA, Elizabeth A; WO2015/171757; (2015); (A1) English, View in Reaxys

10A

Patent; BRISTOL-MYERS SQUIBB COMPANY; JURICA, Elizabeth A.; HONG, Zhenqiu; WO2015/171722; (2015); (A1) English, View in Reaxys

(2R)-13e

Zhao, Xueqing; Pabel, Joerg; Hoefner, Georg C.; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 2; (2013); p. 470 - 484, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.806

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (4) Colour & Other Location Properties

References

yellow

Page/Page column 73

Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; ELLSWORTH, Bruce A; JURICA, Elizabeth A; WO2015/171757; (2015); (A1) English, View in Reaxys

yellow

Page/Page column 94

Patent; BRISTOL-MYERS SQUIBB COMPANY; JURICA, Elizabeth A.; HONG, Zhenqiu; WO2015/171722; (2015); (A1) English, View in Reaxys

white

Paragraph 00469

Patent; BRISTOL-MYERS SQUIBB COMPANY; ELLSWORTH, Bruce, A.; JURICA, Elizabeth, A.; SHI, Jun; EWING, William, R.; YE, Xiang-Yang; WU, Ximao; ZHU, Yeheng; SUN, Chongqing; WO2014/78609; (2014); (A1) English, View in Reaxys

colourless

Zhao, Xueqing; Pabel, Joerg; Hoefner, Georg C.; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 2; (2013); p. 470 - 484, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

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Concentration (Optical Rotatory Power)

1.31 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-18.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Zhao, Xueqing; Pabel, Joerg; Hoefner, Georg C.; Wanner, Klaus T.; Bioorganic and Medicinal Chemistry; vol. 21; nb. 2; (2013); p. 470 - 484, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H NMR (500 MHz, CDC1 ) δ 7.43 - 7.28 (m, 5H), 5.27 - 5.20 (m, 1H), 5.19 - 5.08 (m, 1H), 3 4.92 - 4.78 (m, 1H), 4.07 - 3.88 (m, 2H), 3.81 - 3.56 (m, 3H), 3.03 - 2.87 (m, 1H), 2.61 (dd, J=18.8, 2.6 Hz, 1H).

Location

Page/Page column 73

Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; ELLSWORTH, Bruce A; JURICA, Elizabeth A; WO2015/171757; (2015); (A1) English, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H NMR (500 MHz, CDC13) δ 7.43 - 7.28 (m, 5H), 5.27 - 5.20 (m, 1H), 5.19 - 5.08 (m, 1H), 4.92 - 4.78 (m, 1H), 4.07 - 3.88 (m, 2H), 3.81 - 3.56 (m, 3H), 3.03 - 2.87 (m, 1H), 2.61 (dd, J=18.8, 2.6 Hz, 1H).

Location

Page/Page column 94

Patent; BRISTOL-MYERS SQUIBB COMPANY; JURICA, Elizabeth A.; HONG, Zhenqiu; WO2015/171722; (2015); (A1) English, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Original Text (NMR Spectroscopy)

1H NMR (500 MHz, CDC13)ö 7.43 - 7.28 (m, 5H), 5.27 - 5.20 (m, 1H), 5.19 - 5.08 (m, 1H), 4.92 - 4.78 (m, 1H), 4.07 -3.88 (m, 2H), 3.81 - 3.56 (m, 3H), 3.03 - 2.87 (m, 1H), 2.61 (dd, J=18.8, 2.6 Hz, 1H).

Location

Paragraph 00469

53/232

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References

liquid chromatog- Page/Page colraphy mass spec- umn 73 trometry (LCMS); spectrum

Patent; BRISTOL-MYERS SQUIBB COMPANY; YE, Xiang-Yang; ELLSWORTH, Bruce A; JURICA, Elizabeth A; WO2015/171757; (2015); (A1) English, View in Reaxys

liquid chromatog- Page/Page colraphy mass spec- umn 94 trometry (LCMS); spectrum

Patent; BRISTOL-MYERS SQUIBB COMPANY; JURICA, Elizabeth A.; HONG, Zhenqiu; WO2015/171722; (2015); (A1) English, View in Reaxys

liquid chromatog- Paragraph 00469 raphy mass spectrometry (LCMS); spectrum

Reaxys ID 3556610 View in Reaxys

35/204 CAS Registry Number: 61177-53-5 Chemical Name: (S)-N-Benzyloxycarbonylpyroglutamic acid chloride; N-benzyloxycarbonylpyroglutamic acid chloride; Nbenzyloxycarbonyl-(L)-pyroglutamic acid chloride Linear Structure Formula: C13H12ClNO4 Molecular Formula: C13H12ClNO4 Molecular Weight: 281.696 Type of Substance: heterocyclic InChI Key: RVGICPCXNAMZCA-JTQLQIEISA-N Note:

O N

Substance Label (1) Label References 10

Lessen, Thomas A.; Demko, Donald M.; Weinreb, Steven M.; Tetrahedron Letters; vol. 31; nb. 15; (1990); p. 2105 - 2108, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.727

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

65 - 70

Patent; S. A. Panmedica; US4661512; (1987); (A1) English, View in Reaxys

Reaxys ID 4494351 View in Reaxys

36/204

54/232

2017-11-12 20:29:58

CAS Registry Number: 61177-53-5; 100376-00-9 Linear Structure Formula: C13H12ClNO4 Molecular Formula: C13H12ClNO4 Molecular Weight: 281.696 Type of Substance: heterocyclic InChI Key: RVGICPCXNAMZCA-UHFFFAOYSA-N Note:

O N

Cl L-isomer

Druglikeness (1) 1 of 1

LogP

1.727

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Reaxys ID 5441323 View in Reaxys

37/204 Linear Structure Formula: C13H12ClNO4 Molecular Formula: C13H12ClNO4 Molecular Weight: 281.696 Type of Substance: heterocyclic InChI Key: NZXPOHUNRDALND-NSHDSACASA-N Note:

O N Cl O

Substance Label (1) Label References acid chloride of 7

Sanner, Mark A.; Weigelt, Carolyn; Stansberry, Mary; Killeen, Kelly; Michne, William F.; et al.; Journal of Organic Chemistry; vol. 57; nb. 19; (1992); p. 5264 - 5268, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.146

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Reaxys ID 430755 View in Reaxys

38/204 CAS Registry Number: 51814-18-7 Chemical Name: 3-oxo-pyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-ethyl ester; ethyl N-benzoxycarbonyl-3-oxopyrrolidine-2-carboxylate; N-benzyloxycarbonyl-3-ketoproline ethyl ester Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304

O O N O O

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Type of Substance: heterocyclic InChI Key: TWMLDSILQXQPCW-UHFFFAOYSA-N Note: Substance Label (4) Label References 18

St-Denis; Tak Hang Chan; Canadian Journal of Chemistry; vol. 78; nb. 6; (2000); p. 776 - 783, View in Reaxys

Sibi, Mukund P.; Christensen, James W.; Journal of Organic Chemistry; vol. 64; nb. 17; (1999); p. 6434 6442, View in Reaxys

Sibi; Christensen; Tetrahedron Letters; vol. 31; nb. 40; (1990); p. 5689 - 5692, View in Reaxys

Feil,P.D.; Vercellotti,J.R.; Carbohydrate Research; vol. 31; (1973); p. 311 - 322, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.991

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Boiling Point (1) Boiling Point [°C] 168 - 178

Pressure (Boiling Point) [Torr]

References

0.05

Feil,P.D.; Vercellotti,J.R.; Carbohydrate Research; vol. 31; (1973); p. 311 - 322, View in Reaxys

Refractive Index (1) Refractive Index Wavelength (Refractive Index) [nm]

Temperature (Refractive Index) [°C]

References

1.5184

Feil,P.D.; Vercellotti,J.R.; Carbohydrate Research; vol. 31; (1973); p. 311 - 322, View in Reaxys

589

NMR Spectroscopy (5) 1 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Saito, Tetsuji; Obitsu, Tetsuo; Kondo, Takashi; Matsui, Toshiaki; Nagao, Yuuki; Kusumi, Kensuke; Matsumura, Naoya; Ueno, Sonoko; Kishi, Akihiro; Katsumata, Seishi; Kagamiishi, Yoshifumi; Nakai, Hisao; Toda, Masaaki; Bioorganic and Medicinal Chemistry; vol. 19; nb. 18; (2011); p. 5432 - 5445, View in Reaxys 2 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) St-Denis; Tak Hang Chan; Canadian Journal of Chemistry; vol. 78; nb. 6; (2000); p. 776 - 783, View in Reaxys 3 of 5

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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Solvents (NMR Spectro- CDCl3 scopy) St-Denis; Tak Hang Chan; Canadian Journal of Chemistry; vol. 78; nb. 6; (2000); p. 776 - 783, View in Reaxys 4 of 5

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) St-Denis; Tak Hang Chan; Canadian Journal of Chemistry; vol. 78; nb. 6; (2000); p. 776 - 783, View in Reaxys 5 of 5

Description (NMR Spec- NMR troscopy) Feil,P.D.; Vercellotti,J.R.; Carbohydrate Research; vol. 31; (1973); p. 311 - 322, View in Reaxys

IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

St-Denis; Tak Hang Chan; Canadian Journal of Chemistry; vol. 78; nb. 6; (2000); p. 776 - 783, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Feil,P.D.; Vercellotti,J.R.; Carbohydrate Research; vol. 31; (1973); p. 311 - 322, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

St-Denis; Tak Hang Chan; Canadian Journal of Chemistry; vol. 78; nb. 6; (2000); p. 776 - 783, View in Reaxys

Reaxys ID 6528069 View in Reaxys

39/204 CAS Registry Number: 83507-89-5 Chemical Name: N-<(phenylmethoxy)carbonyl>-4-oxo-(S)-proline ethyl ester; N-benzyloxycarbonyl-4-ketoproline ethyl ester; N-CBz-4-keto-L-proline ethyl ester; N-Cbz-4-keto-L-proline ethyl ester; (2S)-N-Benzyloxycarbonyl-4-oxoproline ethyl ester; N[(phenylmethoxy)carbonyl]-4-oxo-(S)-proline ethyl ester Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304 Type of Substance: heterocyclic InChI Key: UIOORSWZRBWXCD-ZDUSSCGKSA-N Note:

O N O O

Substance Label (3) Label References 1

Anas, Andrea Roxanne J.; Kisugi, Takaya; Umezawa, Taiki; Matsuda, Fuyuhiko; Okino, Tatsufumi; Campitelli, Marc R.; Quinn, Ronald J.; Journal of Natural Products; vol. 75; nb. 9; (2012); p. 1546 - 1552,7, View in Reaxys; Anas, Andrea Roxanne J.; Kisugi, Takaya; Umezawa, Taiki; Matsuda, Fuyuhiko; Campitelli, Marc R.; Quinn, Ronald J.; Okino, Tatsufumi; Journal of Natural Products; vol. 75; nb. 9; (2012); p. 1546 - 1552, View in Reaxys

Slavinskaya; Chipens; Sile; Korchagova; Katkevich; Grigor'eva; Lukevits; Chemistry of Heterocyclic Compounds; vol. 32; nb. 5; (1996); p. 568 - 570, View in Reaxys

Smith, Elizabeth M.; Swiss, Gerald F.; Neustadt, Bernard R.; McNamara, Paul; Gold, Elijah H.; et al.; Journal of Medicinal Chemistry; vol. 32; nb. 7; (1989); p. 1600 - 1606, View in Reaxys

Druglikeness (1)

57/232

2017-11-12 20:29:58

1 of 1

LogP

1.229

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Conformation (1) Object of Investi- References gation Conformation

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys

Crystal Property Description (1) Colour & Other References Properties colourless

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.00 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.5 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-1.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

58/232

2017-11-12 20:29:58

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys Mass Spectrometry (1) Description (Mass Comment (Mass Spectrometry) Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation)

mol peak

References Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys

Reaxys ID 7692859 View in Reaxys

40/204 Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304 Type of Substance: heterocyclic InChI Key: UIOORSWZRBWXCD-UHFFFAOYSA-N Note:

O N O O

Druglikeness (1) 1 of 1

LogP

1.229

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

59/232

2017-11-12 20:29:58

Reaxys ID 8917803 View in Reaxys

41/204 Chemical Name: ethyl N-benzyloxycarbonyl-L-pyroglutamate Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304 Type of Substance: heterocyclic InChI Key: RLGLAAVVDIZYTP-LBPRGKRZSA-N Note:

O N

Substance Label (2) Label References 4(L)

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.81

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.82 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-40.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-44.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys NMR Spectroscopy (4)

60/232

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1 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Location

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys 3 of 4

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

61/232

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Reaxys ID 9341133 View in Reaxys

42/204 Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304 Type of Substance: heterocyclic InChI Key: QTFXSVLQVGQNPA-AAEUAGOBSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

1.932

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 18863562 View in Reaxys

43/204 CAS Registry Number: 1027101-90-1 Chemical Name: N-Cbz-4-keto-D-proline ethyl ester; N-CBz-4keto-D-proline ethyl ester Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304 InChI Key: UIOORSWZRBWXCD-CYBMUJFWSA-N Note:

N O

O O

Substance Label (1) Label References ent-1

Druglikeness (1) 1 of 1

LogP

1.229

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colourless

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

62/232

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Concentration (Optical Rotatory Power)

1.00 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Murphy, Annabel C.; Mitova, Maya I.; Blunt, John W.; Munro, Murray H.G.; Journal of Natural Products; vol. 71; nb. 5; (2008); p. 806 - 809, View in Reaxys

Reaxys ID 20351296 View in Reaxys

44/204 CAS Registry Number: 924907-40-4 Chemical Name: ethyl (R)-5-oxo-N-benzyloxycarbonylpyrrolidine-2-carboxylate Linear Structure Formula: C15H17NO5 Molecular Formula: C15H17NO5 Molecular Weight: 291.304 InChI Key: RLGLAAVVDIZYTP-GFCCVEGCSA-N Note:

O O

N O

Substance Label (2) Label References 4

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

Patent; MERCK PATENT GMBH; US2010/160352; (2010); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.81

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

References He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

63/232

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He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Location

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

He; Griffiths; Wang; Organic and Biomolecular Chemistry; vol. 15; nb. 19; (2017); p. 4241 - 4245, View in Reaxys

Reaxys ID 21649594 View in Reaxys

45/204 CAS Registry Number: 1315591-55-9 Chemical Name: benzyl 3-tert-butoxy-4-oxopyrrolidine-1-carboxylate Linear Structure Formula: C16H21NO4 Molecular Formula: C16H21NO4 Molecular Weight: 291.347 InChI Key: OBNDZSDPPCXENE-UHFFFAOYSA-N Note:

O O N O O

Druglikeness (1) 1 of 1

LogP

2.055

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.84

Lipinski Number

Veber Number

Reaxys ID 19676902 View in Reaxys

46/204

64/232

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CAS Registry Number: 1169845-31-1 Chemical Name: benzyl 3-oxo-5-phenyl-2,3-dihydropyrrol-1carboxylate Linear Structure Formula: C18H15NO3 Molecular Formula: C18H15NO3 Molecular Weight: 293.322 InChI Key: HWMFMZHBKTYJEU-UHFFFAOYSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

3.235

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties orange

supporting information

References Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

270

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

67.8

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys 3 of 4

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

270

Location

supporting information

65/232

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Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys 4 of 4

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Reflection spectrum; Bands

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); EI (Electron impact); Spectrum

References

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys

Reaxys ID 9702323 View in Reaxys

47/204 Chemical Name: benzyl 3-bromo-2-oxopyrrolidine-1-carboxylate Linear Structure Formula: C12H12BrNO3 Molecular Formula: C12H12BrNO3 Molecular Weight: 298.136 Type of Substance: heterocyclic InChI Key: BYYUOWJVCYCHNI-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References 9

Barrett, Roger; Caine, Darren M.; Cardwell, Kevin S.; Cooke, Jason W.B.; Lawrence, Ron M.; Scott, Peter; Sjolin, Asa; Tetrahedron Asymmetry; vol. 14; nb. 22; (2003); p. 3627 - 3631, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.196

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

NMR Spectroscopy (3) 1 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy)

66/232

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Frequency (NMR Spectroscopy) [MHz]

250

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Barrett, Roger; Caine, Darren M.; Cardwell, Kevin S.; Cooke, Jason W.B.; Lawrence, Ron M.; Scott, Peter; Sjolin, Asa; Tetrahedron Asymmetry; vol. 14; nb. 22; (2003); p. 3627 - 3631, View in Reaxys

Reaxys ID 9269576 View in Reaxys

48/204 CAS Registry Number: 470670-71-4 Linear Structure Formula: C15H11NO6 Molecular Formula: C15H11NO6 Molecular Weight: 301.255 Type of Substance: heterocyclic InChI Key: PPJUVRSYKOXCOF-UHFFFAOYSA-N Note:

O N

O O O

Substance Label (1) Label References (+/-)-1g

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.378

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

86.05

67/232

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Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

107 - 108

Solvent (Melting Point)

tert-butyl methyl ether; tetrahydrofuran; petroleum ether

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys Crystal Property Description (1) Colour & Other References Properties light-yellow

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys

Reaxys ID 7438578 View in Reaxys

49/204

68/232

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CAS Registry Number: 176237-43-7 Chemical Name: N-benzyloxycarbonyl-L-pyroglutamic acid isopropyl ester Linear Structure Formula: C16H19NO5 Molecular Formula: C16H19NO5 Molecular Weight: 305.331 Type of Substance: heterocyclic InChI Key: DPCBUEVJYFVJTE-ZDUSSCGKSA-N Note:

O N

Substance Label (1) Label References Schmidt, Ulrich; Braun, Christine; Sutoris, Heinz; Synthesis; nb. 2; (1996); p. 223 - 229, View in Reaxys

9 Druglikeness (1) 1 of 1

LogP

2.27

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-24.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Schmidt, Ulrich; Braun, Christine; Sutoris, Heinz; Synthesis; nb. 2; (1996); p. 223 - 229, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Schmidt, Ulrich; Braun, Christine; Sutoris, Heinz; Synthesis; nb. 2; (1996); p. 223 - 229, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Schmidt, Ulrich; Braun, Christine; Sutoris, Heinz; Synthesis; nb. 2; (1996); p. 223 - 229, View in Reaxys

69/232

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Reaxys ID 14039088 View in Reaxys

50/204 CAS Registry Number: 186770-57-0 Chemical Name: (2S)-N-Benzyloxycarbonyl-4-oxoproline isopropyl ester Linear Structure Formula: C16H19NO5 Molecular Formula: C16H19NO5 Molecular Weight: 305.331 InChI Key: UAHMDSFUWTYDBN-AWEZNQCLSA-N Note:

O O O

O O

Patent-Specific Data (1) Location in Patent References Patent; Degussa Aktiengesellschaft; US5631385; (1997); (A1) English, View in Reaxys

Claim Druglikeness (1) 1 of 1

LogP

1.689

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 26795600 View in Reaxys

51/204 CAS Registry Number: 1584148-42-4 Chemical Name: 1-benzyl 2-methyl 5,5-dimethyl-3-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C16H19NO5 Molecular Formula: C16H19NO5 Molecular Weight: 305.331 InChI Key: FLGOBBVERUFEIM-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 4

Patent; NOVARTIS AG; DILLON, Michael, Patrick; LINDVALL, Mika; POON, Daniel; RAMURTHY, Savithri; RAUNIYAR, Vivek; SHAFER, Cynthia; SUBRAMANIAN, Sharadha; TANNER, Huw; WO2014/47020; (2014); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.445

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Original string data HPLC (High performance liquid chromatography)

Rt = 0.88

Location

References

Page/Page column 50

Mass Spectrometry (1)

70/232

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Description (Mass Location Spectrometry)

References

liquid chromatog- Page/Page colraphy mass spec- umn 50 trometry (LCMS); spectrum

Reaxys ID 9272012 View in Reaxys

52/204 CAS Registry Number: 470670-72-5 Linear Structure Formula: C16H13NO6 Molecular Formula: C16H13NO6 Molecular Weight: 315.282 Type of Substance: heterocyclic InChI Key: WRKHCDSIQSXTQQ-UHFFFAOYSA-N Note:

O N

O O O

Substance Label (1) Label References (+/-)-1h

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.614

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

86.05

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

121 - 122

Solvent (Melting Point)

tert-butyl methyl ether; tetrahydrofuran; 2,2''-azanediyl-bis-ethanol

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys Crystal Property Description (1) Colour & Other References Properties light-yellow

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys

NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

71/232

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Hang, Jianfeng; Li, Hongming; Deng, Li; Organic Letters; vol. 4; nb. 19; (2002); p. 3321 - 3324, View in Reaxys

Reaxys ID 4532980 View in Reaxys

53/204 CAS Registry Number: 96658-38-7 Chemical Name: t-butyl pyrrolin-5-one-2-carboxylate Linear Structure Formula: C17H19NO5 Molecular Formula: C17H19NO5 Molecular Weight: 317.342 Type of Substance: heterocyclic InChI Key: MPIHZLCCIVGUNG-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References 13

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.538

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

86.5 - 87.5

Solvent (Melting Point)

benzene

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys NMR Spectroscopy (2)

72/232

2017-11-12 20:29:58

1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1780 - 1590 cm**(-1)

Shin, Chung-gi; Yonezawa, Yasuchika; Watanabe, Etsuko; Tetrahedron Letters; vol. 26; nb. 1; (1985); p. 85 - 88, View in Reaxys

Reaxys ID 9278300 View in Reaxys

54/204 CAS Registry Number: 477351-70-5 Linear Structure Formula: C17H19NO5 Molecular Formula: C17H19NO5 Molecular Weight: 317.342 Type of Substance: heterocyclic InChI Key: QIXGVDVVPXSEQZ-KBPBESRZSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

2.452

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.165 g/100ml

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Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

7.12

Wavelength (Optical Ro- 589 tatory Power) [nm] Hanessian, Stephen; Margarita, Roberto; Hall, Adrian; Johnstone, Shawn; Tremblay, Martin; Parlanti, Luca; Journal of the American Chemical Society; vol. 124; nb. 45; (2002); p. 13342 - 13343, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hanessian, Stephen; Margarita, Roberto; Hall, Adrian; Johnstone, Shawn; Tremblay, Martin; Parlanti, Luca; Journal of the American Chemical Society; vol. 124; nb. 45; (2002); p. 13342 - 13343, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (IR Spectroscopy)

Bands

Reaxys ID 9792836 View in Reaxys

55/204

74/232

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CAS Registry Number: 394735-51-4 Linear Structure Formula: C17H19NO5 Molecular Formula: C17H19NO5 Molecular Weight: 317.342 Type of Substance: heterocyclic InChI Key: KHJBSKMCAIVKKE-ZFWWWQNUSA-N Note:

O N HO O

Substance Label (2) Label References 23.05

Druglikeness (1) 1 of 1

LogP

1.612

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

130 - 131

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-39.16

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Description (NMR Spec- Spectrum troscopy)

75/232

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Nucleus (NMR Spectroscopy)

Reaxys ID 8709174 View in Reaxys

56/204 CAS Registry Number: 319915-99-6 Chemical Name: (S)-5-Acetoxyacetyl-N-benzoyloxycarbonylpyrrolidin-2-one Linear Structure Formula: C16H17NO6 Molecular Formula: C16H17NO6 Molecular Weight: 319.314 Type of Substance: heterocyclic InChI Key: NJQKVJHYUYCCQG-ZDUSSCGKSA-N Note:

O N O

Substance Label (1) Label References 14

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.034

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

89.98

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

62 - 64

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.25 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-38.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

76/232

2017-11-12 20:29:58

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

62.5

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Boynton, Carole M.; Hewson, Alan T.; Mitchell, Douglas; Journal of the Chemical Society, Perkin Transactions 1; nb. 21; (2000); p. 3599 - 3602, View in Reaxys

Reaxys ID 19504363 View in Reaxys O

57/204 Linear Structure Formula: C16H17NO6 Molecular Formula: C16H17NO6 Molecular Weight: 319.314 InChI Key: NVFJDSFOJCYVQT-UHFFFAOYSA-N Note:

O N

O O

Druglikeness (1) 1 of 1

LogP

1.023

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

89.98

Lipinski Number

Veber Number

77/232

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Reaxys ID 3595597 View in Reaxys

58/204 CAS Registry Number: 125134-29-4 Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 Type of Substance: heterocyclic InChI Key: VLWCTEHZKXFOHR-CYBMUJFWSA-N Note:

O N

Substance Label (2) Label References 16

Marais, Wilhelmina; Holzapfel, Cedric W.; Synthetic Communications; vol. 28; nb. 19; (1998); p. 3681 3691, View in Reaxys

D-17a

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.687

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

49 - 52

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

33.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy)

78/232

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Comment (NMR Spectroscopy)

1H-1H

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys

Reaxys ID 3595598 View in Reaxys

59/204 CAS Registry Number: 81470-51-1 Chemical Name: tert-butyl N-benzyloxycarbonyl-L-pyroglutamate; N2-(benzyloxycarbonyl)-L-pyroglutamic acid 1-tert-butyl ester; 1-benzyl 2-tert-butyl (2S)-5-oxopyrrolidine-1,2-dicarboxylate; (S)-1-benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate; tert-butyl (2S)-N-(benzyloxycarbonyl)pyroglutamate; (S)tert-butyl-N-benzyloxycarbonylpyroglutamate; t-butyl (2S)-Ncarbobenzyloxypyroglutamate Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 Type of Substance: heterocyclic InChI Key: VLWCTEHZKXFOHR-ZDUSSCGKSA-N Note:

O N

Substance Label (17) Label References F2

Patent; Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); (A1) English, View in Reaxys; Patent; MAX-PLANCKGESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); (A1) English, View in Reaxys; Patent; Max-Planck-Gesellschaft zur Forderung der Wissensc haften e.V.; Wang, Yansong; Hausch, Felix; Bischoff, Matthias; Pomplun, Sebastian; (121 pag.); US2017/2003; (2017); (A1) English, View in Reaxys

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix; Organic Letters; vol. 16; nb. 20; (2014); p. 5254 - 5257, View in Reaxys

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys

Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys

Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM; WO2004/50084; (2004); (A2) English, View in Reaxys

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys; Mota, Antonio J.; Chiaroni, Angele; Langlois, Nicole; European Journal of Organic Chemistry; nb. 21; (2003); p. 4187 - 4198, View in Reaxys

Mota, Antonio J.; Langlois, Nicole; Tetrahedron Letters; vol. 44; nb. 6; (2003); p. 1141 - 1143, View in Reaxys

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys

Li; Sakamoto; Kato; Kikugawa; Synthetic Communications; vol. 25; nb. 24; (1995); p. 4045 - 4052, View in Reaxys

cyclised product

Johnstone, Andrew N. C.; Lopatriello, Stefania; North, Michael; Tetrahedron Letters; vol. 35; nb. 34; (1994); p. 6335 - 6338, View in Reaxys

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Dolence, E. Kurt; Minnick, Albert A.; Miller, Marvin J.; Journal of Medicinal Chemistry; vol. 33; nb. 2; (1990); p. 461 - 464, View in Reaxys

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L-17a

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Losse; Raddatz; Naumann; Kossowicz; Pharmazie; vol. 43; nb. 2; (1988); p. 105 - 109, View in Reaxys

Ohta, Tomihisa; Hosoi, Akio; Kimura, Toshihiko; Nozoe, Shigeo; Chemistry Letters; (1987); p. 2091 2094, View in Reaxys

Patent-Specific Data (1) Location in Patent References Page/Page column

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys; Patent; Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.687

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (5) 1 of 5

Melting Point [°C]

43 - 45

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys; Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM; WO2004/50084; (2004); (A2) English, View in Reaxys 2 of 5

Melting Point [°C]

59 - 61

Solvent (Melting Point)

ethyl acetate; hexane

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 5

Melting Point [°C]

53 - 55

Solvent (Melting Point)

ethyl acetate; hexane

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys 4 of 5

Melting Point [°C]

48 - 52

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys 5 of 5

Melting Point [°C]

55 - 57

Losse; Raddatz; Naumann; Kossowicz; Pharmazie; vol. 43; nb. 2; (1988); p. 105 - 109, View in Reaxys Chromatographic Data (6) Chromatographic Original string data

Location

References

Paragraph 0296

Patent; Max-Planck-Gesellschaft zur Forderung der Wissensc haften e.V.; Wang, Yansong; Hausch, Felix; Bischoff, Matthias; Pomplun, Sebastian; (121 pag.); US2017/2003; (2017); (A1) English, View in Reaxys

TLC (Thin layer chromatography)

R&f%: 0.18 (Cyclohexane/EtOAc 3:1, KMnO&4%)

HPLC (High performance liquid chromatography)

CHIRALPAK AD- Paragraph 0239 H, 4.6 x 150 mm, UV 210 nm, hexane/ethanol = 2/1, flow rate 1 mL/

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; FURUUCHI, Takeshi; SAKAMAKI, Yoshiaki; IF2; MORINAKA, Akihiro; EP2857401; (2015); (A1) English, View in Reaxys

80/232

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min., retention time 4.2 min. TLC (Thin layer chromatography)

Rf: 0.18 (Cyclohexane/EtOAc 3:1, KMnO4)

Page/Page column 95

Patent; MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); (A1) English, View in Reaxys

TLC (Thin layer chromatography)

R&f%: 0.18 (Cyclohexane/EtOAc 3:1, KMnO&4%)

Paragraph 0153

Patent; Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); (A1) English, View in Reaxys

supporting information

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix; Organic Letters; vol. 16; nb. 20; (2014); p. 5254 - 5257, View in Reaxys

Paragraph 0188

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys

TLC (Thin layer chromatography) LC (Liquid chromatography)

retention time 4.2 min

Crystal Property Description (10) Colour & Other Location Properties

References

colourless

Paragraph 0295

colourless

Paragraph 0239

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; FURUUCHI, Takeshi; SAKAMAKI, Yoshiaki; IF2; MORINAKA, Akihiro; EP2857401; (2015); (A1) English, View in Reaxys

colourless

Page/Page column 95

Patent; MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); (A1) English, View in Reaxys

colourless

Paragraph 0153

Patent; Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); (A1) English, View in Reaxys

colourless

supporting information

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix; Organic Letters; vol. 16; nb. 20; (2014); p. 5254 - 5257, View in Reaxys

colourless

Paragraph 0188

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys

colorless

Page/Page column 21

Patent; MEIJI SEIKA PHARMA CO., LTD.; US2012/165533; (2012); (A1) English, View in Reaxys

light-brown

Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys

white

Patent; YISSUM RESEARCH DEVELOPMENT COMPANY OF THE HEBREW UNIVERSITY OF JERUSALEM; WO2004/50084; (2004); (A2) English, View in Reaxys

Optical Rotatory Power (12) 1 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.52 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-43.3

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Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

Paragraph 0239

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; FURUUCHI, Takeshi; SAKAMAKI, Yoshiaki; IF2; MORINAKA, Akihiro; EP2857401; (2015); (A1) English, View in Reaxys 2 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.52 g/100ml

Enantiomeric excess [%ee]

99.9

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-43.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

Paragraph 0188

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys 3 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.52 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-43.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

Page/Page column 21

Patent; MEIJI SEIKA PHARMA CO., LTD.; US2012/165533; (2012); (A1) English, View in Reaxys 4 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.05 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

-39.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys

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5 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

37.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys 6 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.75 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-40.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Li; Sakamoto; Kato; Kikugawa; Synthetic Communications; vol. 25; nb. 24; (1995); p. 4045 - 4052, View in Reaxys 7 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-45.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 8 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

5.00 g/100ml

Solvent (Optical Rotatory Power)

dimethylformamide

Optical Rotatory Power [deg]

-39.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

83/232

2017-11-12 20:29:58

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys 9 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

6.71 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-41.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys 10 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.4 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

-40.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys 11 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

4.5 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

-36.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys 12 of 12

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.75 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-20.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

84/232

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Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys NMR Spectroscopy (18) 1 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR

(300 MHz, CDCl3): δ=1.39 (s, 9H, 3×CH3), 1.97-2.70 (m, 4H, 2×CH2), 4.54 (dd, J=9.3, 2.7 Hz, 1H, CH), 5.27 (dd, J=16.2, 12.3 Hz, 2H, CH2), 7.27-7.43 (m, 5H, 5×Ar—H)

Location

Paragraph 0297

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Original Text (NMR Spectroscopy)

13C-NMR (75.5 MHz, CDCl ): δ=25.11, 27.12, 31.23, 59.60, 68.43, 82.76, 128.4, 128.6, 3 128.7, 135.3, 151.1, 170.3, 173.3

Location

Paragraph 0298

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400 MHz, CDCl ) δ 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J = 17.6, 3 9.5, 3.2 Hz, 1H), 2.62 (ddd, J = 17.6, 10.5, 9.5 Hz, 1H), 4.55 (dd, J = 9.5, 2.7 Hz, 1H), 5.25 (d, J = 12.2 Hz, 1H), 5.30 (d, J = 12.2 Hz, 1H), 7.26-7.41 (m, 5H)

Location

Paragraph 0239

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; FURUUCHI, Takeshi; SAKAMAKI, Yoshiaki; IF2; MORINAKA, Akihiro; EP2857401; (2015); (A1) English, View in Reaxys 4 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

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Original Text (NMR Spectroscopy)

1H-NMR (300 MHz, CDCI3): 6 = 1.39 (s, 9 H, 3 x CH3), 1.97—2.70 (m, 4 H, 2 xCH2), 4.54 (dd, J = 9.3, 2.7 Hz, 1 H, CH), 5.27 (dd, J = 16.2, 12.3 Hz, 2 H, CH2), 7.27—7.43(m, 5 H, 5 x Ar-H).

Location

Page/Page column 95

Patent; MAX-PLANCK-GESELLSCHAFT ZUR FÖRDERUNG DER WISSENSCHAFTEN E.V.; WANG, Yansong; HAUSCH, Felix; BISCHOFF, Matthias; POMPLUN, Sebastian; WO2015/110271; (2015); (A1) English, View in Reaxys 5 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Original Text (NMR Spectroscopy)

13C-NMR (75.5 MHz, CDCI3): 6 = 25.11, 27.12, 31.23, 59.60, 68.43, 82.76, 128.4,128.6, 128.7, 135.3, 151.1, 170.3, 173.3.

Location

Page/Page column 95

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

1H-NMR

(300 MHz, CDCl3): δ = 1.39 (s, 9 H, 3 * CH3), 1.97-2.70 (m, 4 H, 2 * CH2), 4.54 (dd, J = 9.3, 2.7 Hz, 1 H, CH), 5.27 (dd, J = 16.2, 12.3 Hz, 2 H, CH 2), 7.27-7.43 (m, 5 H, 5 * Ar-H)

Location

Paragraph 0153

Signals [ppm]

1.39; 1.97 - 2.7; 4.54; 5.27; 7.27 - 7.43

Kind of signal

s, 9 H, 3 * CH&3%; m, 4 H, 2 * CH&2%; dd, J = 9.3, 2.7 Hz, 1 H, CH; dd, J = 16.2, 12.3 Hz, 2 H, CH&2%; m, 5 H, 5 * Ar-H

Patent; Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); (A1) English, View in Reaxys 7 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Original Text (NMR Spectroscopy)

13C-NMR (75.5 MHz, CDCl ): δ = 25.11, 27.12, 31.23, 59.60, 68.43, 82.76, 128.4, 128.6, 3 128.7, 135.3, 151.1, 170.3, 173.3

Location

Paragraph 0153

Signals [ppm]

25.11; 27.12; 31.23; 59.6; 68.43; 82.76; 128.4; 128.6; 128.7; 135.3; 151.1; 170.3; 173.3

Patent; Max-Planck-Gesellschaft zur Förderung der Wissenschaften e.V.; The designation of the inventor has not yet been filed; EP2899192; (2015); (A1) English, View in Reaxys

86/232

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8 of 18

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix; Organic Letters; vol. 16; nb. 20; (2014); p. 5254 - 5257, View in Reaxys 9 of 18

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

75.5

Location

supporting information

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix; Organic Letters; vol. 16; nb. 20; (2014); p. 5254 - 5257, View in Reaxys 10 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

NMR (400 MHz, CDCl3, δ): 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J = 17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J = 17.6, 10.5, 9.5 Hz, 1H), 4.55 (dd, J = 9.5, 2.7 Hz, 1H), 5.25 (d, J = 12.2 Hz, 1H), 5.30 (d, J = 12.2 Hz, 1H), 7.26-7.41 (m, 5H)

Location

Paragraph 0188

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys 12 of 18

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

87/232

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Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

Page/Page column 21

Comment (NMR Spectroscopy)

Signals given

NMR (400 MHz, CDCl3, δ): 1.39 (s, 9H), 2.04 (m, 1H), 2.32 (m, 1H), 2.51 (ddd, J=17.6, 9.5, 3.2 Hz, 1H), 2.62 (ddd, J=176, 10.5, 9.5 Hz, 1H), 4.55 (dd, J=9.5, 2.7 Hz, 1H), 5.25 J=12.2 Hz, 1H), 5.30 (d, J=12.2 Hz, 1H), 7.26-7.41 (m, 5H);

Patent; MEIJI SEIKA PHARMA CO., LTD.; US2012/165533; (2012); (A1) English, View in Reaxys 13 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Jain, Rahul; Organic Preparations and Procedures International; vol. 33; nb. 4; (2001); p. 405 - 409, View in Reaxys; Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys 14 of 18

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys 15 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Deguest, Geoffrey; Bischoff, Laurent; Fruit, Corinne; Marsais, Francis; Tetrahedron Asymmetry; vol. 17; nb. 14; (2006); p. 2120 - 2125, View in Reaxys 16 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys; Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys; Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys; Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 17 of 18

Description (NMR Spec- Spin-spin coupling constants troscopy)

88/232

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Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys; Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys; Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys; Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 18 of 18

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1800 - 1735 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1795 - 1720 cm**(-1)

Dolence, E. Kurt; Lin, Chia-En; Miller, Marvin J.; Payne, Shelley M.; Journal of Medicinal Chemistry; vol. 34; nb. 3; (1991); p. 956 - 968, View in Reaxys 3 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Comment (IR Spectroscopy)

1785 - 1735 cm**(-1)

Kolasa, Teodozyj; Miller, Marvin J.; Journal of Organic Chemistry; vol. 55; nb. 6; (1990); p. 1711 - 1721, View in Reaxys 4 of 4

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1800 - 1740 cm**(-1)

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys Mass Spectrometry (5) Description (Mass Location Spectrometry)

References

89/232

2017-11-12 20:29:58

spectrum

Paragraph 0239

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; FURUUCHI, Takeshi; SAKAMAKI, Yoshiaki; IF2; MORINAKA, Akihiro; EP2857401; (2015); (A1) English, View in Reaxys

supporting inforhigh resolution mass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); liquid chromatography mass spectrometry (LCMS); spectrum

Bischoff, Matthias; Sippel, Claudia; Bracher, Andreas; Hausch, Felix; Organic Letters; vol. 16; nb. 20; (2014); p. 5254 - 5257, View in Reaxys

electrospray ionisation (ESI); liquid chromatography mass spectrometry (LCMS); spectrum

spectrum

Paragraph 0188

Patent; Meiji Seika Pharma Co., Ltd.; ABE, Takao; OKUE, Masayuki; SAKAMAKI, Yoshiaki; EP2657234; (2013); (A1) English, View in Reaxys

spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys

Reaxys ID 7491604 View in Reaxys

60/204 Chemical Name: (+/-)-1-Benzyloxycarbonyl-5-(tert-butoxycarbonyl)pyrrolidin-2-one; (S)-1-benzyl 2-tert-butyl 5-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 Type of Substance: heterocyclic InChI Key: VLWCTEHZKXFOHR-UHFFFAOYSA-N Note:

O N

Substance Label (2) Label References (+/-)-5

Mota, Antonio J.; Chiaroni, Angele; Langlois, Nicole; European Journal of Organic Chemistry; nb. 21; (2003); p. 4187 - 4198, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.687

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

87 - 89

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NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Evans, P. Andrew; Holmes, Andrew B.; McGeary, Ross P.; Nadin, Alan; Russell, Keith; O'Hanlon, Peter J.; Pearson, Neil D.; Journal of the Chemical Society - Perkin Transactions 1; nb. 2; (1996); p. 123 - 138, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Evans, P. Andrew; Holmes, Andrew B.; McGeary, Ross P.; Nadin, Alan; Russell, Keith; O'Hanlon, Peter J.; Pearson, Neil D.; Journal of the Chemical Society - Perkin Transactions 1; nb. 2; (1996); p. 123 - 138, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CCl4

Comment (IR Spectroscopy)

3120 - 1730 cm**(-1)

Reaxys ID 8216015 View in Reaxys

61/204

91/232

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CAS Registry Number: 147489-27-8 Chemical Name: (2S)-4-oxo-1-phenylmethoxycarbonylpyrrolidine-2-carboxylic acid tert-butyl ester; (2S)-4-oxopyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester; (2S)-4-oxypyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-tertbutyl ester; 1-benzyl 2-(tert-butyl) (S)-4-oxopyrrolidine-1,2-dicarboxylate; N-benzyloxycarbonyl-4-oxo-L-proline tert-butyl ester Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 Type of Substance: heterocyclic InChI Key: UOZXRTSYHFCTJZ-AWEZNQCLSA-N Note:

O O N O

Substance Label (8) Label References 4

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys

Sugase, Kenji; Horikawa, Manabu; Sugiyama, Masako; Ishiguro, Masaji; Journal of Medicinal Chemistry; vol. 47; nb. 2; (2004); p. 489 - 492, View in Reaxys

Patent; Schafmeister, Christian E.; US2004/77879; (2004); (A1) English, View in Reaxys

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys

VIII

Yelin; Onoprienko; Kudelina; Miroshnikov; Russian Journal of Bioorganic Chemistry; vol. 26; nb. 11; (2000); p. 774 - 783, View in Reaxys

Wessig, Pablo; Synlett; nb. 9; (1999); p. 1465 - 1467, View in Reaxys

Yelin; Onoprienko; Russian Journal of Bioorganic Chemistry; vol. 24; nb. 9; (1998); p. 594 - 598, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.106

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (2) Colour & Other Location Properties yellow

supporting information

yellow

References Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys

Optical Rotatory Power (3) 1 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

dimethyl sulfoxide

Optical Rotatory Power [deg]

-7.6

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Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

5.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys 3 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Sugase, Kenji; Horikawa, Manabu; Sugiyama, Masako; Ishiguro, Masaji; Journal of Medicinal Chemistry; vol. 47; nb. 2; (2004); p. 489 - 492, View in Reaxys NMR Spectroscopy (11) 1 of 11

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 11

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

93/232

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Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 3 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys 4 of 11

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys 5 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys 6 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Sugase, Kenji; Horikawa, Manabu; Sugiyama, Masako; Ishiguro, Masaji; Journal of Medicinal Chemistry; vol. 47; nb. 2; (2004); p. 489 - 492, View in Reaxys 7 of 11

Nucleus (NMR Spectroscopy)

Coupling Nuclei

94/232

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Sugase, Kenji; Horikawa, Manabu; Sugiyama, Masako; Ishiguro, Masaji; Journal of Medicinal Chemistry; vol. 47; nb. 2; (2004); p. 489 - 492, View in Reaxys 8 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Sugase, Kenji; Horikawa, Manabu; Sugiyama, Masako; Ishiguro, Masaji; Journal of Medicinal Chemistry; vol. 47; nb. 2; (2004); p. 489 - 492, View in Reaxys 9 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys 10 of 11

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys 11 of 11

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

75.4

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys IR Spectroscopy (2)

95/232

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1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys; Jung, Jae-Chul; Avery, Mitchell A.; Tetrahedron Asymmetry; vol. 17; nb. 17; (2006); p. 2479 - 2486, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

film

Sugase, Kenji; Horikawa, Manabu; Sugiyama, Masako; Ishiguro, Masaji; Journal of Medicinal Chemistry; vol. 47; nb. 2; (2004); p. 489 - 492, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

spectrum; electron impact (EI)

Levins, Christopher G.; Schafmeister, Christian E.; Journal of the American Chemical Society; vol. 125; nb. 16; (2003); p. 4702 - 4703, View in Reaxys

Reaxys ID 9345756 View in Reaxys

62/204 Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 Type of Substance: heterocyclic InChI Key: IVKPZKCYQIPJCD-ZFWWWQNUSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

3.07

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 10176568 View in Reaxys

63/204

96/232

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CAS Registry Number: 870097-43-1 Chemical Name: (R)-4-oxo-pyrrolidine-1,2-dicarboxylic acid 1benzyl ester 2-tert-butyl ester; 1-benzyl 2-(tert-butyl) (R)-4-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 Type of Substance: heterocyclic InChI Key: UOZXRTSYHFCTJZ-CQSZACIVSA-N Note:

O O N O

Substance Label (2) Label References 10

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

sc3

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.106

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties yellow

supporting information

References Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

dimethyl sulfoxide

Optical Rotatory Power [deg]

10.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

97/232

2017-11-12 20:29:58

Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 2 of 7

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys 3 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 4 of 7

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

350

Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 5 of 7

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

98/232

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Frequency (NMR Spectroscopy) [MHz]

300

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 6 of 7

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Comment (NMR Spectroscopy)

ambient temperature

Levins, Christopher G.; Schafmeister, Christian E.; Journal of Organic Chemistry; vol. 70; nb. 22; (2005); p. 9002 - 9008, View in Reaxys 7 of 7

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Frequency (NMR Spectroscopy) [MHz]

75.4

Comment (NMR Spectroscopy)

ambient temperature

References

high resolution supporting informass spectrome- mation try (HRMS); electrospray ionisation (ESI); timeof-flight mass spectra (TOFMS); spectrum

Cheong, Jae Eun; Pfeiffer, Conrad T.; Northrup, Justin D.; Parker, Matthew F.L.; Schafmeister, Christian E.; Tetrahedron Letters; vol. 57; nb. 44; (2016); p. 4882 - 4884, View in Reaxys

Reaxys ID 14040514 View in Reaxys

64/204 CAS Registry Number: 186770-58-1 Chemical Name: (2S)-N-Benzyloxycarbonyl-4-oxoproline n-butyl ester Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 InChI Key: SCUTXSVXZJVMAX-HNNXBMFYSA-N Note:

O O O

O O

Patent-Specific Data (1) Location in Patent References Claim

Patent; Degussa Aktiengesellschaft; US5631385; (1997); (A1) English, View in Reaxys

Druglikeness (1)

99/232

2017-11-12 20:29:58

1 of 1

LogP

2.156

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 26795780 View in Reaxys

65/204 CAS Registry Number: 1584148-76-4 Chemical Name: 1-benzyl 2-methyl 5-ethyl-5-methyl-3-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 InChI Key: QTMYHBMCMXQWBY-UHFFFAOYSA-N Note:

O N

O O

Substance Label (1) Label References 25

Druglikeness (1) 1 of 1

LogP

1.803

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Original string data HPLC (High performance liquid chromatography)

Rt = 0.94

Mass Spectrometry (1) Description (Mass Location Spectrometry) liquid chromatog- Page/Page colraphy mass spec- umn 64 trometry (LCMS); spectrum

Location

References

Page/Page column 64

References Patent; NOVARTIS AG; DILLON, Michael, Patrick; LINDVALL, Mika; POON, Daniel; RAMURTHY, Savithri; RAUNIYAR, Vivek; SHAFER, Cynthia; SUBRAMANIAN, Sharadha; TANNER, Huw; WO2014/47020; (2014); (A1) English, View in Reaxys

Reaxys ID 29406683 View in Reaxys

66/204

100/232

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Chemical Name: 1-benzyl 2-(tert-butyl) 3-oxopyrrolidine-1,2-dicarboxylate; 1-benzyl 2-(tert-butyl)-3-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C17H21NO5 Molecular Formula: C17H21NO5 Molecular Weight: 319.357 InChI Key: YHHXGFYPEQWRAA-UHFFFAOYSA-N Note:

O N O

O O

Substance Label (2) Label References Compound (h)

Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys

Doebelin, Christelle; He, Yuanjun; Kamenecka, Theodore M.; Tetrahedron Letters; vol. 57; nb. 50; (2016); p. 5658 - 5660, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.868

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

54 - 56

Location

Page/Page column 58

Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties yellow

Page/Page column 58

References Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

1H NMR (400MHz ,CHLOROFORM-d) δ = 7.44 - 7.28 (m, 5 H), 5.30 - 5.09 (m, 2 H), 4.53 - 4.43 (m, 1 H), 4.06 - 3.91 (m, 1 H), 3.91 - 3.79 (m, 1 H), 2.72 - 2.65 (m, 2 H), 1.48 - 1.37 (m, 9 H)

Location

Page/Page column 58

Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy)

101/232

2017-11-12 20:29:58

Frequency (NMR Spectroscopy) [MHz]

101

Original Text (NMR Spectroscopy)

13C NMR (101 MHz , CDC1 ) δ = 204.4, 203.9, 164.9, 164.8, 154.6, 154.6, 136.1, 135.8, 3 128.5, 128.4, 128.2, 128.1, 128.0, 127.9, 83.3, 83.2, 67.5, 66.2, 66.0, 42.1, 36.8, 36.1, 27.8, 27.7

Location

Page/Page column 58

Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Doebelin, Christelle; He, Yuanjun; Kamenecka, Theodore M.; Tetrahedron Letters; vol. 57; nb. 50; (2016); p. 5658 - 5660, View in Reaxys 4 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Location

supporting information

Doebelin, Christelle; He, Yuanjun; Kamenecka, Theodore M.; Tetrahedron Letters; vol. 57; nb. 50; (2016); p. 5658 - 5660, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Original Text (IR Spectroscopy)

IR: 1766, 1735, 1701, 1402, 1152, 1100

Location

Page/Page column 58

Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Page/Page column 58

Patent; EOLAS THERAPEUTICS, INC.; KAMENECKA, Theodore M.; HE, Yuanjun; (105 pag.); WO2016/25669; (2016); (A1) English, View in Reaxys

high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

supporting information

Doebelin, Christelle; He, Yuanjun; Kamenecka, Theodore M.; Tetrahedron Letters; vol. 57; nb. 50; (2016); p. 5658 - 5660, View in Reaxys

102/232

2017-11-12 20:29:58

Reaxys ID 8428598 View in Reaxys

67/204 Linear Structure Formula: C19H17NO4 Molecular Formula: C19H17NO4 Molecular Weight: 323.348 Type of Substance: heterocyclic InChI Key: OOCLCTQBGFGBKZ-INIZCTEOSA-N Note:

O O

Substance Label (1) Label References 14b

Li, Baoqing; Franck, Richard W.; Bioorganic and Medicinal Chemistry Letters; vol. 9; nb. 17; (1999); p. 2629 - 2634, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.502

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

63.68

Lipinski Number

Veber Number

Reaxys ID 29717682 View in Reaxys

68/204 Chemical Name: benzyl (R)-3-(benzyloxy)-4-oxopyrrolidine-1carboxylate Linear Structure Formula: C19H19NO4 Molecular Formula: C19H19NO4 Molecular Weight: 325.364 InChI Key: KVYFORRVSFDKAJ-GOSISDBHSA-N Note:

N O

Substance Label (1) Label References 3a

Druglikeness (1) 1 of 1

LogP

2.465

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.84

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy)

103/232

2017-11-12 20:29:58

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Si, Chong; Fales, Kevin R.; Torrado, Alicia; Frimpong, Kwame; Kaoudi, Talbi; Vandeveer, Harold George; Njoroge, F. George; Journal of Organic Chemistry; vol. 81; nb. 10; (2016); p. 4359 - 4363, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) high resolution mass spectrometry (HRMS); electrospray ionisation (ESI); spectrum

Reaxys ID 7826839 View in Reaxys

69/204 CAS Registry Number: 192311-42-5 Linear Structure Formula: C18H21NO5 Molecular Formula: C18H21NO5 Molecular Weight: 331.368 Type of Substance: heterocyclic InChI Key: CQNGCVYLUKPACU-UHFFFAOYSA-N Note:

O O N O O

Substance Label (1) Label References scheme 2

Belanger, Guillaume; Hong, Fang-Tsao; Overman, Larry E.; Rogers, Bruce N.; Tellew, John E.; Trenkle, William C.; Journal of Organic Chemistry; vol. 67; nb. 22; (2002); p. 7880 - 7883, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.056

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

104/232

2017-11-12 20:29:58

Reaxys ID 9718313 View in Reaxys

70/204 CAS Registry Number: 701261-84-9 Chemical Name: (2S,4S)-4-but-3-enyl-5-oxopyrrolidine-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester Linear Structure Formula: C18H21NO5 Molecular Formula: C18H21NO5 Molecular Weight: 331.368 Type of Substance: heterocyclic InChI Key: BXXIIAAOYAQAOV-GJZGRUSLSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

3.021

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.25 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-19.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Hanessian, Stephen; Tremblay, Martin; Petersen, Jens F. W.; Journal of the American Chemical Society; vol. 126; nb. 19; (2004); p. 6064 - 6071, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Hanessian, Stephen; Tremblay, Martin; Petersen, Jens F. W.; Journal of the American Chemical Society; vol. 126; nb. 19; (2004); p. 6064 - 6071, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

105/232

2017-11-12 20:29:58

Hanessian, Stephen; Tremblay, Martin; Petersen, Jens F. W.; Journal of the American Chemical Society; vol. 126; nb. 19; (2004); p. 6064 - 6071, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Hanessian, Stephen; Tremblay, Martin; Petersen, Jens F. W.; Journal of the American Chemical Society; vol. 126; nb. 19; (2004); p. 6064 - 6071, View in Reaxys

Reaxys ID 9790532 View in Reaxys

71/204 CAS Registry Number: 757994-66-4 Chemical Name: N-benzyloxycarbonyl-3α-(3-methylbuten-3yl)-4-oxo-L-proline Linear Structure Formula: C18H21NO5 Molecular Formula: C18H21NO5 Molecular Weight: 331.368 Type of Substance: heterocyclic InChI Key: NXFNNJBRHZEXAA-HOCLYGCPSA-N Note:

O O N OH

Substance Label (1) Label References 10

Druglikeness (1) 1 of 1

LogP

2.136

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties brown

Reaxys ID 9791560 View in Reaxys

72/204

106/232

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CAS Registry Number: 757994-70-0 Chemical Name: N-benzyloxycarbonyl-3-(2-methylallyl)-4-oxoL-proline methyl ester Linear Structure Formula: C18H21NO5 Molecular Formula: C18H21NO5 Molecular Weight: 331.368 Type of Substance: heterocyclic InChI Key: BYQGKEAFLVQGRD-WMCAAGNKSA-N Note:

O O N O

Substance Label (1) Label References 12

Druglikeness (1) 1 of 1

LogP

1.933

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 14450041 View in Reaxys

73/204 CAS Registry Number: 394735-50-3 Linear Structure Formula: C18H21NO5 Molecular Formula: C18H21NO5 Molecular Weight: 331.368 InChI Key: BYQGKEAFLVQGRD-HOCLYGCPSA-N Note:

O O

N O O

Substance Label (1) Label References 23.04

Druglikeness (1) 1 of 1

LogP

1.933

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 21341854 View in Reaxys

74/204

107/232

2017-11-12 20:29:58

CAS Registry Number: 1301240-85-6 Linear Structure Formula: C18H23NO5 Molecular Formula: C18H23NO5 Molecular Weight: 333.384 InChI Key: SQAPUNUAQDENTN-JSGCOSHPSA-N Note:

O O

N O O

Druglikeness (1) 1 of 1

LogP

2.98

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-40.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

26.4

Location

supporting information

Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

108/232

2017-11-12 20:29:58

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Location

supporting information

Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys Mass Spectrometry (2) Description (Mass Location Spectrometry)

References

ESI (Electrospray ionisation); Spectrum

supporting information

Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys

HRMS (High resolution mass spectrometry); Spectrum

supporting information

Li, Wenhua; Yu, Shouyun; Jin, Mingzhi; Xia, Hongguang; Ma, Dawei; Tetrahedron Letters; vol. 52; nb. 17; (2011); p. 2124 - 2127, View in Reaxys

Reaxys ID 5773393 View in Reaxys

O O

75/204 CAS Registry Number: 82379-40-6 Linear Structure Formula: C16H17NO7 Molecular Formula: C16H17NO7 Molecular Weight: 335.313 Type of Substance: heterocyclic InChI Key: ZJCGXNHRAMNLPF-LBPRGKRZSA-N Note:

O N

Substance Label (2) Label References interm. a) to 6

Altmann, Karl-Heinz; Tetrahedron Letters; vol. 34; nb. 48; (1993); p. 7721 - 7724, View in Reaxys

Chorev; Rubini; Gilon; Wormser; Selinger; Journal of Medicinal Chemistry; vol. 26; nb. 2; (1983); p. 129 135, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.431

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

99.21

Lipinski Number

Veber Number

109/232

2017-11-12 20:29:58

Reaxys ID 9346814 View in Reaxys

76/204 Linear Structure Formula: C19H17NO5 Molecular Formula: C19H17NO5 Molecular Weight: 339.348 Type of Substance: heterocyclic InChI Key: SCANRGJFXYTHKX-WBVHZDCISA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

2.446

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 9789022 View in Reaxys

77/204 CAS Registry Number: 757994-56-2 Chemical Name: N-(benzyloxycarbonyl)-3-(3-methylbuten-2yl)-4-oxo-L-proline methyl ester Linear Structure Formula: C19H23NO5 Molecular Formula: C19H23NO5 Molecular Weight: 345.395 Type of Substance: heterocyclic InChI Key: NVSIVTSDTSJPKU-LWKPJOBUSA-N Note:

O O N O

Substance Label (1) Label References 5

Druglikeness (1) 1 of 1

LogP

2.457

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 500781 View in Reaxys

78/204

110/232

2017-11-12 20:29:58

CAS Registry Number: 78816-93-0 Chemical Name: 1-benzyl 2-(2,5-dioxopyrrolidin-1-yl) pyrrolidine-1,2-dicarboxylate; benzyl (S)-2-{[(2,5-dioxo-1-pyrrolidinyl)oxy]carbonyl}pyrrolidine-1-carboxylate; Z-L-proline hydroxysuccinimide ester Linear Structure Formula: C17H18N2O6 Molecular Formula: C17H18N2O6 Molecular Weight: 346.34 Type of Substance: heterocyclic InChI Key: BDNYCEKWUBRCBJ-UHFFFAOYSA-N Note:

O N O

N O

Substance Label (2) Label References 3g

Kaname; Mashige; Yoshifuji; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 5; (2001); p. 531 - 536, View in Reaxys

Z-Pro-N-hydroxysuccinimidester

Anderson et al.; Journal of the American Chemical Society; vol. 86; (1964); p. 1839,1840, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.755

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

85 - 87

Patent; Jasuda Naokhiko et al.; JP47115332; (1976); Ref. Zh., Khim.; vol. 13; nb. 016p; (1977), View in Reaxys 2 of 2

Melting Point [°C]

Solvent (Melting Point)

propan-2-ol

Anderson et al.; Journal of the American Chemical Society; vol. 86; (1964); p. 1839,1840, View in Reaxys Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-55

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Jasuda Naokhiko et al.; JP47115332; (1976); Ref. Zh., Khim.; vol. 13; nb. 016p; (1977), View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

dioxane

Optical Rotatory Power [deg]

-54

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Anderson et al.; Journal of the American Chemical Society; vol. 86; (1964); p. 1839,1840, View in Reaxys

111/232

2017-11-12 20:29:58

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

Frequency (NMR Spectroscopy) [MHz]

Kaname; Mashige; Yoshifuji; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 5; (2001); p. 531 - 536, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Kaname; Mashige; Yoshifuji; Chemical and Pharmaceutical Bulletin; vol. 49; nb. 5; (2001); p. 531 - 536, View in Reaxys

Reaxys ID 4580440 View in Reaxys

79/204 CAS Registry Number: 3397-33-9 Chemical Name: Z-proline N-hydroxysuccinimide ester; Z-ProOSu Linear Structure Formula: C17H18N2O6 Molecular Formula: C17H18N2O6 Molecular Weight: 346.34 Type of Substance: heterocyclic InChI Key: BDNYCEKWUBRCBJ-ZDUSSCGKSA-N Note:

O N O

N O

Substance Label (7) Label References 4f

Escorihuela, Jorge; Altava, Belen; Burguete, M. Isabel; Luis, Santiago V.; Tetrahedron; vol. 69; nb. 2; (2013); p. 551 - 558, View in Reaxys

Duvall, Jeremy R.; Wu, Fanghui; Snider, Barry B.; Journal of Organic Chemistry; vol. 71; nb. 22; (2006); p. 8579 - 8590, View in Reaxys

Snider, Barry B.; Duvall, Jeremy R.; Organic Letters; vol. 7; nb. 20; (2005); p. 4519 - 4522, View in Reaxys

Z-Pro-OSu

Stefanowicz, P.; Siemion, I. Z.; Polish Journal of Chemistry; vol. 66; nb. 1; (1992); p. 111 - 118, View in Reaxys

21e

Sawayama; Tsukamoto; Sasagawa; Nishimura; Yamamoto; Deguchi; Takeyama; Hosoki; Chemical and Pharmaceutical Bulletin; vol. 37; nb. 9; (1989); p. 2417 - 2422, View in Reaxys

Nr. 15

Appel, Rolf; Glaesel, Ursula; Chemische Berichte; vol. 113; nb. 11; (1980); p. 3511 - 3516, View in Reaxys

<6>

Wuensch; Moroder; Gemeiner; et al.; Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie; vol. 35; nb. 7; (1980); p. 911 - 921, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.755

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

112/232

2017-11-12 20:29:58

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

89 - 90

Il'ina, A. V.; Davidovich, Yu. A.; Rogozhin, S. V.; Moiseenkov, A. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; (1984); p. 1067 - 1070; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 5; (1984); p. 1163 - 1165, View in Reaxys Optical Rotatory Power (3) 1 of 3

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-54.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Jaoudai, Mahmoud; Martinez, Jean; Castro, Bertrand; Journal of Organic Chemistry; vol. 52; nb. 12; (1987); p. 2364 - 2367, View in Reaxys 2 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

dioxane

Optical Rotatory Power [deg]

-55.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2 g/100ml

Solvent (Optical Rotatory Power)

dioxane

Optical Rotatory Power [deg]

-54.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Appel, Rolf; Glaesel, Ursula; Chemische Berichte; vol. 113; nb. 11; (1980); p. 3511 - 3516, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy)

113/232

2017-11-12 20:29:58

Larden, Dale W.; Andrew Cheung; Tetrahedron; vol. 55; nb. 11; (1999); p. 3265 - 3276, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Larden, Dale W.; Andrew Cheung; Tetrahedron; vol. 55; nb. 11; (1999); p. 3265 - 3276, View in Reaxys

Reaxys ID 15140112 View in Reaxys

CAS Registry Number: 104055-24-5 Chemical Name: N-benzyloxycarbonyl-D-proline N-hydroxysuccinimide ester Linear Structure Formula: C17H18N2O6 Molecular Formula: C17H18N2O6 Molecular Weight: 346.34 InChI Key: BDNYCEKWUBRCBJ-CYBMUJFWSA-N Note:

O N

80/204

Druglikeness (1) 1 of 1

LogP

0.755

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Reaxys ID 9348357 View in Reaxys

81/204 CAS Registry Number: 531539-18-1 Chemical Name: (2S)-1-benzyloxycarbonyl-5-oxo-pyrrolidine-2-carboxylic acid 2-(3-methyl-oxetan-3-yl-methyl) ester Linear Structure Formula: C18H21NO6 Molecular Formula: C18H21NO6 Molecular Weight: 347.368 Type of Substance: heterocyclic InChI Key: BKZBBPMYKJOFEP-AWEZNQCLSA-N Note:

O N

O O

Substance Label (1) Label References 7a

Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.614

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

82.14

Lipinski Number

114/232

2017-11-12 20:29:58

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

3.0 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

-19.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

200

Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys 3 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Herdeis, Claus; Kelm, Bernd; Tetrahedron; vol. 59; nb. 2; (2003); p. 217 - 229, View in Reaxys

115/232

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Reaxys ID 31019913 View in Reaxys

82/204 Chemical Name: 1-[4-(acetyloxy)benzyl] 2-ethyl 5-oxopyrrolidine-1,2-dicarboxylate Linear Structure Formula: C17H19NO7 Molecular Formula: C17H19NO7 Molecular Weight: 349.34 InChI Key: JLXPKMOPDPFYBF-AWEZNQCLSA-N Note:

O O

N O O

Substance Label (1) Label References 5

Patent; THE JOHNS HOPKINS UNIVERSITY; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I.; SLUSHER, Barbara; RAIS, Rana; TENORA, Lukas; MAJER, Pavel; JANCARIK, Andrej; NEDELCOVYCH, Mike; (208 pag.); WO2017/23774; (2017); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.595

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

99.21

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other Location Properties colourless

Page/Page column 85

References Patent; THE JOHNS HOPKINS UNIVERSITY; INSTITUTE OF ORGANIC CHEMISTRY AND BIOCHEMISTRY AS CR V.V.I.; SLUSHER, Barbara; RAIS, Rana; TENORA, Lukas; MAJER, Pavel; JANCARIK, Andrej; NEDELCOVYCH, Mike; (208 pag.); WO2017/23774; (2017); (A1) English, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.298 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-30.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

Page/Page column 85

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy)

116/232

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Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Location

Page/Page column 85

NMR (400 MHz, CDC13): 1.16 (3H, t, J = 7.2), 1.99 - 2.06 (1H, m), 2.25 (3H, s), 2.28 2.36 (1H, m), 2.42 - 2.50 (1H, m), 2.55 - 2.64 (1H, m), 4.11 (1H, qd, J= 7.1, 2.6), 4.62 (1H, dd, J= 9.4, 2.7), 5.16 (1H, d, J= 12.4), 4.25 (1H, d, J= 12.4), 7.02 - 7.05 (2H, m), 7.35 7.39 (2H, m).

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Original Text (NMR Spectroscopy)

13C NMR (101 MHz, CDC1 ): 14.02, 21.08, 21.79, 30.99, 58.74, 61.82, 67.58, 121.75, 3 129.46, 132.62, 150.70, 150.83, 169.28, 170.97, 172.93.

Location

Page/Page column 85

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

chloroform

Original Text (IR Spectroscopy)

IR (CHC13): 2968 w, 2942 vw, 2876 vw, 1797 s, 1753 vs, 1717 s, sh, 1609 w, 1597 vw, 1510 m, 1476 vw, 1463 w, 1450 w, 1447 w5 1421 w, 1402 w, sh, 1380 m, 1372 m, 1303 s, 1288 s, 1259 m, 1198 vs, 1166 s, 1107 vw, 1045 m, 1019 m, 1012 m, sh, 913 w, 846 w, 596 w cm-1.

Location

Page/Page column 85; 86

References

electrospray ionisation (ESI); spectrum

Page/Page column 86

electrospray ionisation (ESI); high resolution mass spectrometry (HRMS); spectrum

Page/Page column 86

Reaxys ID 19676918 View in Reaxys

83/204

117/232

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CAS Registry Number: 1169845-34-4 Chemical Name: benzyl 2-benzyl-3-oxo-5-propyl-2,3-dihydropyrrole-1-carboxylate Linear Structure Formula: C22H23NO3 Molecular Formula: C22H23NO3 Molecular Weight: 349.43 InChI Key: UQNGDTYKOIRBFM-UHFFFAOYSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

4.311

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

270

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

67.8

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys 3 of 4

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Frequency (NMR Spectroscopy) [MHz]

270

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys 4 of 4

Description (NMR Spec- Spectrum troscopy)

118/232

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Nucleus (NMR Spectroscopy)

13C

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Reflection spectrum; Bands

Location

supporting information

References

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys

Reaxys ID 19676919 View in Reaxys

84/204 Chemical Name: benzyl 2-benzyl-3-oxo-5-propyl-2,3-dihydropyrrole-1-carboxylate Linear Structure Formula: C22H23NO3 Molecular Formula: C22H23NO3 Molecular Weight: 349.43 InChI Key: UQNGDTYKOIRBFM-HXUWFJFHSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

4.311

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Reaxys ID 19676920 View in Reaxys

85/204 CAS Registry Number: 1169845-43-5 Chemical Name: benzyl 2-benzyl-3-oxo-5-propyl-2,3-dihydropyrrole-1-carboxylate Linear Structure Formula: C22H23NO3 Molecular Formula: C22H23NO3 Molecular Weight: 349.43 InChI Key: UQNGDTYKOIRBFM-FQEVSTJZSA-N Note:

N O

119/232

2017-11-12 20:29:58

Druglikeness (1) 1 of 1

LogP

4.311

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Enantiomeric excess [%ee]

Solvent (Optical Rotatory Power)

dichloromethane

Optical Rotatory Power [deg]

-55.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Gouault, Nicolas; Le Roch, Myriam; Cornee, Carole; David, Michele; Uriac, Philippe; Journal of Organic Chemistry; vol. 74; nb. 15; (2009); p. 5614 - 5617, View in Reaxys

Reaxys ID 5124209 View in Reaxys

86/204 CAS Registry Number: 104754-54-3 Chemical Name: benzyl N-benzyloxycarbonyl-Δ3-pyrrolin-2one-5-carboxylate Linear Structure Formula: C20H17NO5 Molecular Formula: C20H17NO5 Molecular Weight: 351.359 Type of Substance: heterocyclic InChI Key: OHTIWYNLUXJSDY-UHFFFAOYSA-N Note:

O N

Substance Label (1) Label References 45

Baldwin, Jack E.; Cha, Jin K.; Kruse, Lawrence I.; Tetrahedron; vol. 41; nb. 22; (1985); p. 5241 - 5260, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.948

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

120/232

2017-11-12 20:29:58

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Cha, Jin K.; Kruse, Lawrence I.; Tetrahedron; vol. 41; nb. 22; (1985); p. 5241 - 5260, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Baldwin, Jack E.; Cha, Jin K.; Kruse, Lawrence I.; Tetrahedron; vol. 41; nb. 22; (1985); p. 5241 - 5260, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3000 - 1730 cm**(-1)

Baldwin, Jack E.; Cha, Jin K.; Kruse, Lawrence I.; Tetrahedron; vol. 41; nb. 22; (1985); p. 5241 - 5260, View in Reaxys

Reaxys ID 47784 View in Reaxys

87/204

CAS Registry Number: 71389-33-8 Chemical Name: dibenzyl (2S)-5-oxotetrahydro-1H-pyrrole-1,2dicarboxylate; N1,5-bis(benzyloxycarbonyl)-2-pyrrolidinone; Nbenzyloxycarbonylpyroglutamate benzyl ester; CBZ-L-pyroglutamic acid benzyl ester; 1-benzyloxycarbonyl-5-oxo-L-prolinebenzyl ester; 1-Benzyloxycarbonyl-5-oxo-L-prolin-benzylester Linear Structure Formula: C20H19NO5 Molecular Formula: C20H19NO5 Molecular Weight: 353.375 Type of Substance: heterocyclic InChI Key: ARURAOJLLAPYOP-KRWDZBQOSA-N Note:

O N

Substance Label (2) Label References 8

Katritzky, Alan R.; Angrish, Parul; Todadze, Ekaterina; Ghiviriga, Ion; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 21; (2007); p. 6000 - 6002, View in Reaxys

Thompson, Mark J.; Mekhalfia, Abdelaziz; Hornby, David P.; Blackburn, G. Michael; Journal of Organic Chemistry; vol. 64; nb. 20; (1999); p. 7467 - 7473, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

121/232

2017-11-12 20:29:58

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (5) 1 of 5

Melting Point [°C]

109 - 112

Solvent (Melting Point)

dichloromethane

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 2 of 5

Melting Point [°C]

109 - 111

Solvent (Melting Point)

CH2Cl2; hexane

Katritzky, Alan R.; Angrish, Parul; Todadze, Ekaterina; Ghiviriga, Ion; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 21; (2007); p. 6000 - 6002, View in Reaxys 3 of 5

Melting Point [°C]

110.5 - 111.5

Solvent (Melting Point)

benzene; light petroleum

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys 4 of 5

Melting Point [°C]

107 - 108

Danishefsky,S. et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4385 - 4386, View in Reaxys 5 of 5

Melting Point [°C]

110

Berenbom; White; Journal of the American Chemical Society; vol. 71; (1949); p. 2246, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties white

supporting information

References Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 - 6299, View in Reaxys

Optical Rotatory Power (6) 1 of 6

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-51

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 2 of 6

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.0066 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

-0.11

122/232

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Wavelength (Optical Ro- 589 tatory Power) [nm] Thompson, Mark J.; Mekhalfia, Abdelaziz; Hornby, David P.; Blackburn, G. Michael; Journal of Organic Chemistry; vol. 64; nb. 20; (1999); p. 7467 - 7473, View in Reaxys 3 of 6

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.972 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-40.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys 4 of 6

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.1 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-47.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 5 of 6

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-40.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Danishefsky,S. et al.; Journal of the American Chemical Society; vol. 101; (1979); p. 4385 - 4386, View in Reaxys 6 of 6

Type (Optical Rotatory Power)

[alpha]

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-39.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Berenbom; White; Journal of the American Chemical Society; vol. 71; (1949); p. 2246, View in Reaxys NMR Spectroscopy (9)

123/232

2017-11-12 20:29:58

1 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 2 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

101

Location

supporting information

Kitulagoda, James E.; Palmelund, Anders; Aggarwal, Varinder K.; Tetrahedron; vol. 66; nb. 33; (2010); p. 6293 6299, View in Reaxys 3 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

Katritzky, Alan R.; Angrish, Parul; Todadze, Ekaterina; Ghiviriga, Ion; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 21; (2007); p. 6000 - 6002, View in Reaxys 4 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Katritzky, Alan R.; Angrish, Parul; Todadze, Ekaterina; Ghiviriga, Ion; Bioorganic and Medicinal Chemistry Letters; vol. 17; nb. 21; (2007); p. 6000 - 6002, View in Reaxys 5 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Thompson, Mark J.; Mekhalfia, Abdelaziz; Hornby, David P.; Blackburn, G. Michael; Journal of Organic Chemistry; vol. 64; nb. 20; (1999); p. 7467 - 7473, View in Reaxys

124/232

2017-11-12 20:29:58

6 of 9

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

250

Thompson, Mark J.; Mekhalfia, Abdelaziz; Hornby, David P.; Blackburn, G. Michael; Journal of Organic Chemistry; vol. 64; nb. 20; (1999); p. 7467 - 7473, View in Reaxys 7 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys; August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys 8 of 9

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys; August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys 9 of 9

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys IR Spectroscopy (2) 1 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1790 - 1705 cm**(-1)

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys 2 of 2

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1800 - 1750 cm**(-1)

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

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Reaxys ID 4557945 View in Reaxys

88/204 CAS Registry Number: 71389-33-8 Chemical Name: Z-L-pGlu-OBzl Linear Structure Formula: C20H19NO5 Molecular Formula: C20H19NO5 Molecular Weight: 353.375 Type of Substance: heterocyclic InChI Key: ARURAOJLLAPYOP-UHFFFAOYSA-N Note:

O N

L-isomer

Substance Label (2) Label References Table 1, entry a-e

Ohta, Tomihisa; Kimura, Toshihiko; Sato, Nobuaki; Nozoe, Shigeo; Tetrahedron Letters; vol. 29; nb. 34; (1988); p. 4303 - 4304, View in Reaxys

Pettit, George R.; Nelson, Paul S.; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 741 - 744, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.375 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-41.3

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Pettit, George R.; Nelson, Paul S.; Journal of Organic Chemistry; vol. 48; nb. 5; (1983); p. 741 - 744, View in Reaxys

Reaxys ID 8340703 View in Reaxys

89/204 CAS Registry Number: 84969-25-5 Chemical Name: 4-Keto-1-[(phenylmethoxy)carbonyl]-L-proline benzyl ester; (2S)-4-oxopyrrolidine-1,2-dicarboxylic acid dibenzyl ester; (2S)-N-Benzyloxycarbonyl-4-oxoproline benzyl ester Linear Structure Formula: C20H19NO5 Molecular Formula: C20H19NO5 Molecular Weight: 353.375 Type of Substance: heterocyclic InChI Key: OVYDXOQNKHZEDW-SFHVURJKSA-N Note:

O N O O

Substance Label (2)

126/232

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Label

References

Ganorkar, Rakesh; Natarajan, Amarnath; Mamai, Ahmed; Madalengoitia, Jose S.; Journal of Organic Chemistry; vol. 71; nb. 13; (2006); p. 5004 - 5007, View in Reaxys

Wessig, Pablo; Synlett; nb. 9; (1999); p. 1465 - 1467, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.516

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Patent; Degussa Aktiengesellschaft; US5631385; (1997); (A1) English, View in Reaxys

2 of 2

Patent; E. R. Squibb and Sons, Inc.; US4734508; (1988); (A1) English, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Patent; E. R. Squibb and Sons, Inc.; US4734508; (1988); (A1) English, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Ganorkar, Rakesh; Natarajan, Amarnath; Mamai, Ahmed; Madalengoitia, Jose S.; Journal of Organic Chemistry; vol. 71; nb. 13; (2006); p. 5004 - 5007, View in Reaxys 2 of 2

Description (NMR Spec- Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Ganorkar, Rakesh; Natarajan, Amarnath; Mamai, Ahmed; Madalengoitia, Jose S.; Journal of Organic Chemistry; vol. 71; nb. 13; (2006); p. 5004 - 5007, View in Reaxys

Reaxys ID 15827711 View in Reaxys

90/204 CAS Registry Number: 1028851-78-6 Chemical Name: methyl (+/-)-(N-benzyloxycarbonyl)-3-oxo-5phenylpyrrolidine-2-carboxylate Linear Structure Formula: C20H19NO5 Molecular Formula: C20H19NO5 Molecular Weight: 353.375 InChI Key: SCEQGJJLKFWMKU-UHFFFAOYSA-N Note:

O O N O O

Substance Label (1) Label References 19

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys

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Druglikeness (1) 1 of 1

LogP

2.381

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys

Reaxys ID 19630725 View in Reaxys

91/204 Linear Structure Formula: C20H19NO5 Molecular Formula: C20H19NO5 Molecular Weight: 353.375 InChI Key: DHBYXSFRGLRNOF-KRWDZBQOSA-N Note:

O O

N O

Druglikeness (1) 1 of 1

LogP

2.154

H Bond Donors

128/232

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H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 27589095 View in Reaxys

92/204 Linear Structure Formula: C16H20BrNO3 Molecular Formula: C16H20BrNO3 Molecular Weight: 354.244 InChI Key: FDNLXHKDZQAMDL-VYIIXAMBSA-N Note:

O O

N O

Substance Label (1) Label References 14

Druglikeness (1) 1 of 1

LogP

2.906

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Original string data LC (Liquid chromatography)

Location

LC-MS tR = 1.772 Paragraph 00115 mm in 2 mm chromatography,

Mass Spectrometry (1) Description (Mass Location Spectrometry) liquid chromatog- Paragraph 00115 raphy mass spectrometry (LCMS); electrospray ionisation (ESI); spectrum

References Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); (A1) English, View in Reaxys

Reaxys ID 7496472 View in Reaxys

93/204

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Chemical Name: benzyl (2S,3S)-N-(benzyloxycarbonyl)-<3(2)H>pyroglutamate; benzyl (2S,3S)-N-(benzyloxycarbonyl)-(3(2)H)pyroglutamate Linear Structure Formula: C20H18DNO5 Molecular Formula: C20H19NO5 Molecular Weight: 354.367 Type of Substance: heterocyclic InChI Key: ARURAOJLLAPYOP-AXSIHZQASA-N Note:

O N

O 2

Druglikeness (1) 1 of 1

LogP

3.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys

Reaxys ID 7497647 View in Reaxys

94/204 Chemical Name: benzyl (2S,3R)-N-(benzyloxycarbonyl)-<2,3(2)H2>pyroglutamate; benzyl (2S,3R)-N-(benzyloxycarbonyl)(2,3-(2)H2)pyroglutamate Linear Structure Formula: C20H17D2NO5 Molecular Formula: C20H19NO5 Molecular Weight: 355.359 Type of Substance: heterocyclic InChI Key: ARURAOJLLAPYOP-XXIATBRYSA-N Note:

O O

O N O

Druglikeness (1) 1 of 1

LogP

3.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

130/232

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TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

August, Ryan A.; Khan, Jeffrey A.; Moody, Claire M.; Young, Douglas W.; Journal of the Chemical Society - Perkin Transactions 1; nb. 6; (1996); p. 507 - 514, View in Reaxys

Reaxys ID 943285 View in Reaxys

CAS Registry Number: 40291-26-7; 144232-85-9 Linear Structure Formula: C17H16N2O7 Molecular Formula: C17H16N2O7 Molecular Weight: 360.323 Type of Substance: heterocyclic InChI Key: LZNYDJDSWANAND-UHFFFAOYSA-N Note:

O N

95/204

Substance Label (1) Label References A12.015

Patent; Ansorge, Siegfried; Bank, Ute; Nordhoff, Karsten; Taeger, Michael; Striggow, Frank; US2007/37752; (2007); (A1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

110.29

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

131 - 132

Patent; Abbott; DE2406543; (1974); Chem.Abstr.; vol. 87; nb. 39849, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

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Optical Rotatory Power [deg]

-23

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Patent; Abbott; DE2406543; (1974); Chem.Abstr.; vol. 87; nb. 39849, View in Reaxys Medchem (3) 1 of 3

Target Name

Aminopeptidase N

Target Synonyms

alanine aminopeptidase; alanyl aminopeptidase; alpha-aminoacylpeptide hydrolase (aminopeptidase n); aminopeptidase ey; aminopeptidase m; aminopeptidase n; anpep; ap-m; ap-n; apde; apn; apn1 (aminopeptidase n); apn2 (aminopeptidase n); b0932; bapn; bn1008_2224; bn17_07931; capn; cc_2481; cd13; cryia(c) receptor (aminopeptidase n); cs35_0939; dp32_05460; econih1_05915; ecs1015; el75_2810; el79_2886; el80_2824; ers451419_03194; fapn; gp130 (aminopeptidase n); gp150 (aminopeptidase n); hapn; hi_1614; hus2011_1014; hw43_08385; jd73_08885; jw0915; kidney zn peptidase; kzp; l102360; lap (aminopeptidase n); lap-1 (aminopeptidase n); lap1 (aminopeptidase n); ll0305; llmg_0319; lys-ap; lysyl aminopeptidase (aminopeptidase n); mapn; membrane glycoprotein h11; membrane protein p161; microsomal aminopeptidase; myeloid plasma membrane glycoprotein cd13; papn; pd07_27610; pepn; pgd_02358; pu06_12065; pu15_21620; pu21_19010; pu33_10650; pu38_22460; pu53_07620; pu69_14440; pu71_03785; pu73_07160; rapn; rbapn; rr31_05070; sg46_0939; sg47_0939; sg48_0945; sy51_05290; uc21_08485; uc41_00705; un86_22035; un87_22155; un88_15200; un89_26440; un90_25315; un91_21335; un92_26625; vm92_11800

Target, Subunit, Species Aminopeptidase N Target Mutant/Chimera Details

Aminopeptidase N:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

943285View in Reaxys

Substance Name

A1.007

Measurement Parameter

IC50

Unit

µM

Quantitative value

8.4

Measurement pX

5.08

Concomitants: Compound name

Ala-Ala-Rhodamine

Concomitants: Compound role

SUB

Patent; Ansorge, Siegfried; Bank, Ute; Nordhoff, Karsten; Taeger, Michael; Striggow, Frank; US2007/37752; (2007); (A1) English, View in Reaxys 2 of 3

Target Name

Aminopeptidase N

Target Synonyms

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sy51_05290; uc21_08485; uc41_00705; un86_22035; un87_22155; un88_15200; un89_26440; un90_25315; un91_21335; un92_26625; vm92_11800 Target, Subunit, Species Aminopeptidase N

3 of 3

Target Mutant/Chimera Details

Aminopeptidase N:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against Alanyl aminopeptidase

Substance RN

943285View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

7.5

Measurement pX

5.12

Target Name

Aminopeptidase N

Target Synonyms

Target, Subunit, Species Aminopeptidase N Target Mutant/Chimera Details

Aminopeptidase N:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound against Alanyl aminopeptidase

Substance RN

943285View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

8.4

Measurement pX

5.08

Reaxys ID 5157479 View in Reaxys

96/204

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CAS Registry Number: 40291-26-7 Chemical Name: N-benzyloxycarbonyl-L-pyroglutamic acid Nhydroxysuccinimido ester; Z-L-pyroglutamic acid succinimido ester; Z-pGlu-ONSu; Z-pGlu-OSu; Z-Glp-OSu; Z-Pyr-OSu; Nbenzyloxycarbonyl-L-pyroglutamic acid N-hydroxysuccinimide ester Linear Structure Formula: C17H16N2O7 Molecular Formula: C17H16N2O7 Molecular Weight: 360.323 Type of Substance: heterocyclic InChI Key: LZNYDJDSWANAND-LBPRGKRZSA-N Note:

O O O

N O

O N

Substance Label (1) Label References 4

Yajima; Minamitake; Funakoshi; Akaji; Oishi; Akazawa; Segawa; Nakata; Inoue; Chemical and Pharmaceutical Bulletin; vol. 29; nb. 9; (1981); p. 2587 - 2591, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

110.29

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Larden, Dale W.; Andrew Cheung; Tetrahedron; vol. 55; nb. 11; (1999); p. 3265 - 3276, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Larden, Dale W.; Andrew Cheung; Tetrahedron; vol. 55; nb. 11; (1999); p. 3265 - 3276, View in Reaxys

Reaxys ID 5776553 View in Reaxys

97/204 CAS Registry Number: 144232-85-9 Chemical Name: Z-Pyr-OSu; N-benzyloxycarbonyl-D-pyroglutamic acid-N-hydroxysuccinimide ester Linear Structure Formula: C17H16N2O7 Molecular Formula: C17H16N2O7 Molecular Weight: 360.323 Type of Substance: heterocyclic InChI Key: LZNYDJDSWANAND-GFCCVEGCSA-N Note:

O O O

N O

O N

Druglikeness (1)

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1 of 1

LogP

0.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

110.29

Lipinski Number

Veber Number

Reaxys ID 498321 View in Reaxys

O O O O

98/204 CAS Registry Number: 24051-32-9 Chemical Name: 1-Benzyloxycarbonyl-2-oxo-5,5-diethoxycarbonyl-Δ3-pyrrolin Linear Structure Formula: C18H19NO7 Molecular Formula: C18H19NO7 Molecular Weight: 361.351 Type of Substance: heterocyclic InChI Key: UPCIDQGLABCHJS-UHFFFAOYSA-N Note:

O N

Substance Label (2) Label References XVIII

Kishida,Y.; Terada,A.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2417 - 2423, View in Reaxys

I, R=Z, R %1&=CO2Et

Patent; Sankyo Co.; JP6915644; (1966); Chem.Abstr.; vol. 71; nb. 124224m; (1969), View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.044

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

99.21

Lipinski Number

Veber Number

Boiling Point (2) Boiling Point [°C]

Pressure (Boiling Point) [Torr]

References

160 - 165

0.0001

Kishida,Y.; Terada,A.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2417 2423, View in Reaxys

150 - 155

0.0001

Patent; Sankyo Co.; JP6915644; (1966); Chem.Abstr.; vol. 71; nb. 124224m; (1969), View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Kishida,Y.; Terada,A.; Chemical and Pharmaceutical Bulletin; vol. 17; (1969); p. 2417 - 2423, View in Reaxys

Reaxys ID 4592263 View in Reaxys

99/204

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Chemical Name: Z-L-Prolin-N-hydroxysuccinimidester Linear Structure Formula: C17H18N2O7 Molecular Formula: C17H18N2O7 Molecular Weight: 362.339 Type of Substance: heterocyclic InChI Key: KYIXIGOKEXDCGV-UEWDXFNNSA-N Note:

O O

O O O

Druglikeness (1) 1 of 1

LogP

1.124

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

113.45

Lipinski Number

Veber Number

Reaxys ID 8442097 View in Reaxys

100/204 CAS Registry Number: 96522-33-7 Chemical Name: Benzyloxycarbonyl-L-4-hydroxyprolin-N-hydroxysuccinimidester Linear Structure Formula: C17H18N2O7 Molecular Formula: C17H18N2O7 Molecular Weight: 362.339 Type of Substance: heterocyclic InChI Key: UIYMPWVMLYSZRV-OLZOCXBDSA-N Note:

O N O

N O

Substance Label (1) Label References Z-L-Hyp-OSu

Lifferth, Axel; Bahner, Isabel; Lackner, Helmut; Schaefer, Martina; Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences; vol. 54; nb. 5; (1999); p. 681 - 691, View in Reaxys

Druglikeness (1) 1 of 1

LogP

-0.275

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

113.45

Lipinski Number

Veber Number

Reaxys ID 8715284 View in Reaxys

101/204

O O

Linear Structure Formula: C18H21NO7 Molecular Formula: C18H21NO7 Molecular Weight: 363.367 Type of Substance: heterocyclic InChI Key: LZYYNTNMVSQDHR-AWEZNQCLSA-N Note:

136/232

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Druglikeness (1) 1 of 1

LogP

3.086

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

99.21

Lipinski Number

Veber Number

Reaxys ID 13248614 View in Reaxys

102/204 Chemical Name: N -benzyloxycarbonylproline N -hydroxysuccinimide; N-benzyloxycarbonylproline N-hydroxysuccinimide Linear Structure Formula: C4H5NO3*C13H15NO4 Molecular Formula: C4H5NO3*C13H15NO4 Molecular Weight: 364.355 InChI Key: LHODKVKYMAHRBQ-UHFFFAOYSA-N Note:

N OH O

O O

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

124.45

Lipinski Number

Veber Number

Reaxys ID 19711128 View in Reaxys

103/204 CAS Registry Number: 1099818-39-9 Linear Structure Formula: C21H21NO5 Molecular Formula: C21H21NO5 Molecular Weight: 367.401 InChI Key: MIGKGGOBAJCQDY-ROUUACIJSA-N Note:

O O

N O O

Druglikeness (1) 1 of 1

LogP

3.125

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

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Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.8 g/100ml

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

47.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Location

supporting information

Sun, Wei; Nikolovska-Coleska, Zaneta; Qin, Dongguang; Sun, Haiying; Yang, Chao-Yie; Bai, Longchuang; Qiu, Su; Wang, You; Ma, Dawei; Wang, Shaomeng; Journal of Medicinal Chemistry; vol. 52; nb. 3; (2009); p. 593 596, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Description (NMR Spec- COSY (Correlation Spectroscopy); Spectrum troscopy) Nucleus (NMR Spectroscopy)

Location

supporting information

Description (NMR Spec- NOESY (Nuclear Overhauser Enhanced Spectroscopy); Spectrum troscopy)

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Nucleus (NMR Spectroscopy)

Location

supporting information

Description (IR Spectroscopy)

Bands

Location

supporting information

Comment (IR Spectroscopy)

film

References

ESI (Electrospray ionisation); Spectrum

Sun, Wei; Nikolovska-Coleska, Zaneta; Qin, Dongguang; Sun, Haiying; Yang, ChaoYie; Bai, Longchuang; Qiu, Su; Wang, You; Ma, Dawei; Wang, Shaomeng; Journal of Medicinal Chemistry; vol. 52; nb. 3; (2009); p. 593 - 596, View in Reaxys

supporting information

Reaxys ID 31621967 View in Reaxys

Linear Structure Formula: C21H21NO5 Molecular Formula: C21H21NO5 Molecular Weight: 367.401 InChI Key: WOUGKSAYMLFPTK-QAPCUYQASA-N Note:

N O

104/204

Substance Label (1) Label References 3

Patent; Shanghai Modern Pharmaceutical Co., Ltd.; Shanghai Pharmaceutical Industry Institute; Huang Wenwu; Shan Xiaoyan; Chen Xudong; Hu Erying; Zhang Jie; (14 pag.); CN106810485; (2017); (A) Chinese, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.39

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Location Spectrometry) spectrum

Paragraph 0040

References Patent; Shanghai Modern Pharmaceutical Co., Ltd.; Shanghai Pharmaceutical Industry Institute; Huang Wenwu; Shan Xiaoyan; Chen Xudong; Hu Erying; Zhang Jie; (14 pag.); CN106810485; (2017); (A) Chinese, View in Reaxys

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Reaxys ID 2310426 View in Reaxys

105/204 CAS Registry Number: 56694-32-7 Linear Structure Formula: C21H25NO5 Molecular Formula: C21H25NO5 Molecular Weight: 371.433 Type of Substance: heterocyclic InChI Key: KTXLMJBMTHURAF-UHFFFAOYSA-N Note:

O O O N

O O

Druglikeness (1) 1 of 1

LogP

3.29

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

57 - 59

Saito,T.; Chemistry Letters; (1975); p. 729 - 732, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-63.6

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Saito,T.; Chemistry Letters; (1975); p. 729 - 732, View in Reaxys

Reaxys ID 4825184 View in Reaxys

106/204 CAS Registry Number: 135524-03-7 Chemical Name: Benzyl (2R,4S,1'R)-2-(tert-butyl)-4-<hydroxy(2-furyl)methyl>-5-oxo-3-oxazolidinecarboxylate; Benzyl (2R,4S,1'R)-2-(tert-butyl)-4-[hydroxy(2-furyl)methyl]-5-oxo-3-oxazolidinecarboxylate Linear Structure Formula: C20H23NO6 Molecular Formula: C20H23NO6 Molecular Weight: 373.406 Type of Substance: heterocyclic InChI Key: KDSNTHXAZPOGFO-LZLYRXPVSA-N Note:

O N

H O

O O

Substance Label (1) Label References 17

Blaser, Denis; Seebach, Dieter; Liebigs Annalen der Chemie; nb. 10; (1991); p. 1067 - 1078, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.206

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H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

89.21

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.37 g/100ml

Solvent (Optical Rotatory Power)

CHCl3; ethanol

Optical Rotatory Power [deg]

121

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Comment (Optical Rota- Ratio of solvents: 99:1 tory Power) Blaser, Denis; Seebach, Dieter; Liebigs Annalen der Chemie; nb. 10; (1991); p. 1067 - 1078, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Blaser, Denis; Seebach, Dieter; Liebigs Annalen der Chemie; nb. 10; (1991); p. 1067 - 1078, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Blaser, Denis; Seebach, Dieter; Liebigs Annalen der Chemie; nb. 10; (1991); p. 1067 - 1078, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3620 - 1045 cm**(-1)

Blaser, Denis; Seebach, Dieter; Liebigs Annalen der Chemie; nb. 10; (1991); p. 1067 - 1078, View in Reaxys

Reaxys ID 9350607 View in Reaxys

107/204

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Linear Structure Formula: C19H16ClNO5 Molecular Formula: C19H16ClNO5 Molecular Weight: 373.793 Type of Substance: heterocyclic InChI Key: ACBFZOCRHBLCAO-WBVHZDCISA-N Note:

O N O O

Druglikeness (1) 1 of 1

LogP

3.068

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

83.91

Lipinski Number

Veber Number

Reaxys ID 24277328 View in Reaxys

108/204 Linear Structure Formula: C19H22N2O6 Molecular Formula: C19H22N2O6 Molecular Weight: 374.393 InChI Key: MNXJRDIQDPVSAJ-VYDXJSESSA-N Note:

O O

N O

N O O

Druglikeness (1) 1 of 1

LogP

1.118

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

85.38

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

Papain

Target Synonyms

papain; papaya proteinase i; ppi

Target, Subunit, Species Papain Target Mutant/Chimera Details

Papain:Wild

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

24277328View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.49

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2 of 2

Measurement pX

6.31

Concomitants: Compound RN

1721408; 506008

Concomitants: Compound name

(+)-Cysteine; DMSO

Concomitants: Compound role

COM; SLV

Target Name

Cathepsin B [Rattus norvegicus]

Target Synonyms

cathepsin b; cathepsin b1; ctsb; rsg-2

Target Uniprot ID

p00787

Target PDB ID

1cpj; 1cte; 1mir; 1the

Target, Subunit, Species Cathepsin B [Rattus norvegicus] Target Mutant/Chimera Details

Cathepsin B [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Bioassay Category

In Vitro (Efficacy)

Bioassay Name

Enzymology inhibition

Substance RN

24277328View in Reaxys

Substance Name

Measurement Parameter

IC50

Unit

µM

Quantitative value

0.44

Measurement pX

6.36

Concomitants: Compound RN

506008; 1719757

Concomitants: Compound name

DMSO; Dithiothreitol; CBZ-Phe-Arg-AMC

Concomitants: Compound role

SLV; COM; SUB

Reaxys ID 25978211 View in Reaxys

109/204 Linear Structure Formula: C19H22N2O6 Molecular Formula: C19H22N2O6 Molecular Weight: 374.393 InChI Key: MNXJRDIQDPVSAJ-CKDQBVIESA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

1.118

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

85.38

Lipinski Number

143/232

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Veber Number

Medchem (2) 1 of 2

Target Name

Papain

Target Synonyms

papain; papaya proteinase i; ppi

Target, Subunit, Species Papain

2 of 2

Target Mutant/Chimera Details

Papain:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound was determined against papain

Substance RN

25978211View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.49

Measurement pX

6.31

Target Name

Cathepsin B

Target Synonyms

app secretase; apps; bcsb (cathepsin b); catb-10270; catb-16; catb-1674; catb-16d; catb-1852; catb-1874; catb-2744; catb-3098; catb-348; catb-3483; catb-84; catb-912; cathepsin b; cathepsin b1; cpsb (cathepsin b); ctsb; ddb_g0283921; loc100159070; qcce-13673; rsg-2

Target, Subunit, Species Cathepsin B Target Mutant/Chimera Details

Cathepsin B:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Inhibitory concentration of the compound was determined against cathepsin B

Substance RN

25978211View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.44

Measurement pX

6.36

Reaxys ID 26055456 View in Reaxys

110/204

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Linear Structure Formula: C19H22N2O6 Molecular Formula: C19H22N2O6 Molecular Weight: 374.393 InChI Key: MNXJRDIQDPVSAJ-ISXOHVOVSA-N Note:

O O

N O

Druglikeness (1) 1 of 1

LogP

1.118

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

85.38

Lipinski Number

Veber Number

Medchem (2) 1 of 2

Target Name

Cathepsin B [Rattus norvegicus]

Target Synonyms

cathepsin b; cathepsin b1; ctsb; rsg-2

Target Uniprot ID

p00787

Target PDB ID

1cpj; 1cte; 1mir; 1the

Target, Subunit, Species Cathepsin B [Rattus norvegicus] Target Mutant/Chimera Details

Cathepsin B [Rattus norvegicus]:Wild

Target Species (Bioactivity)

Rattus norvegicus

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration against rat Cathepsin B using N-CBZ-Phe-Arg-AMC as substrate (5 mM) upon incubation with 56 mM sodium acetate pH 5. for 10 min at RT in pH 5.1 with the compound (10 uL) dissolved in DMSO

Biological Species/NCBI Rattus norvegicus ID

2 of 2

Substance RN

26055456View in Reaxys

Substance Dose

10 µL

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.44

Measurement pX

6.36

Concomitants: Compound name

N-CBZ-Phe-Arg-AMC

Concomitants: Compound role

SUB

Target Name

Papain

Target Synonyms

papain; papaya proteinase i; ppi

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Target, Subunit, Species Papain Target Mutant/Chimera Details

Papain:Wild

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

In vitro inhibitory concentration against Papain using N-CBZ-Pro-Phe-Arg-pNA as substrate (10 mM) upon incubation with 0.2 M potassium phosphate 10 min at RT in pH 6.5 with the compound (10 uL) dissolved in DMSO

Substance RN

26055456View in Reaxys

Measurement Parameter

IC50

Unit

µM

Qualitative value

Quantitative value

0.49

Measurement pX

6.31

Concomitants: Compound name

N-CBZ-Pro-Phe-Arg-pNA; N-CBZ-Pro-Phe-Arg-pNA

Concomitants: Compound role

COM; SUB

Reaxys ID 15142657 View in Reaxys

111/204 CAS Registry Number: 75486-16-7 Chemical Name: 1-Carbobenzyloxy-2-carbo-t-butoxy-5-carbomethoxy-3-pyrrolidinone Linear Structure Formula: C19H23NO7 Molecular Formula: C19H23NO7 Molecular Weight: 377.394 InChI Key: SQHQGWRIUJTOJZ-UHFFFAOYSA-N Note:

O O

Druglikeness (1) 1 of 1

LogP

1.674

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

99.21

Lipinski Number

Veber Number

Reaxys ID 15134387 View in Reaxys

112/204 Chemical Name: 4-Keto-1-[(phenylmethoxy)carbonyl]-L-proline pyrrolidine amide Linear Structure Formula: C5H10N2O*C13H13NO5 Molecular Formula: C5H10N2O*C13H13NO5 Molecular Weight: 377.397 InChI Key: UPUFBZXFZOWODF-MERQFXBCSA-N Note:

O O

H 2N

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Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

130.24

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

109 - 111

Patent; E. R. Squibb and Sons, Inc.; US4734508; (1988); (A1) English, View in Reaxys

Reaxys ID 5143814 View in Reaxys

113/204 CAS Registry Number: 127949-79-5 Chemical Name: t-butyl (2S)-1-benzyloxycarbonyl-4-(1-hydroxypropyl)pyroglutamate Linear Structure Formula: C20H27NO6 Molecular Formula: C20H27NO6 Molecular Weight: 377.437 Type of Substance: heterocyclic InChI Key: WPXGCWXUCJTAHD-PCKAHOCUSA-N Note:

O N

O OH

Substance Label (1) Label References 2b

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.095

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.5 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-11.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

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NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3510 - 1735 cm**(-1)

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Reaxys ID 15648808 View in Reaxys

114/204 CAS Registry Number: 1017576-15-6 Linear Structure Formula: C5H7NO3*C14H20N2O2 Molecular Formula: C5H7NO3*C14H20N2O2 Molecular Weight: 377.44 InChI Key: FWXBWKHLGAGOED-ZUVSFCSHSA-N Note:

O O

H N

NH 2

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

121.96

Lipinski Number

Veber Number

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Reaxys ID 5144240 View in Reaxys

115/204

CAS Registry Number: 78420-34-5 Linear Structure Formula: C21H19NO6 Molecular Formula: C21H19NO6 Molecular Weight: 381.385 Type of Substance: heterocyclic InChI Key: IVAPZZVLHJHYKC-SFHVURJKSA-N Note:

O N

Substance Label (2) Label References 4

Danishefsky, Samuel; Morris, Joel; Clizbe, Lane A.; Journal of the American Chemical Society; vol. 103; nb. 6; (1981); p. 1602 - 1604, View in Reaxys

Danishefsky, Samuel; Morris, Joel; Clizbe, Lane A.; Heterocycles; vol. 15; nb. 2; (1981); p. 1205 - 1208, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.304

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Reaxys ID 15827715 View in Reaxys Cl

116/204 CAS Registry Number: 1028851-80-0 Chemical Name: methyl (+/-)-(N-benzyloxycarbonyl)-3-oxo-4chloro-5-phenylpyrrolidine-2-carboxylate Linear Structure Formula: C20H18ClNO5 Molecular Formula: C20H18ClNO5 Molecular Weight: 387.82 InChI Key: OMTQYRHNUIJWEW-UHFFFAOYSA-N Note:

O O N O

Substance Label (1) Label References 20

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.658

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties

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light-yellow

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat liquid

Davis, Franklin A.; Bowen, Kerisha A.; Xu, He; Velvadapu, Venkata; Tetrahedron; vol. 64; nb. 19; (2008); p. 4174 - 4182, View in Reaxys

Reaxys ID 27589161 View in Reaxys O

N O

117/204 Linear Structure Formula: C19H18BrNO3 Molecular Formula: C19H18BrNO3 Molecular Weight: 388.261 InChI Key: JOSASVOZGKQITA-UHFFFAOYSA-N Note:

O Br

Substance Label (1) Label References 17

Druglikeness (1) 1 of 1

LogP

3.769

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

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Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Original string data LC (Liquid chromatography)

LC-MS tR = 1.01 mm in 1.5 mm chromatography

Mass Spectrometry (1) Description (Mass Location Spectrometry)

Location

References

Paragraph 00119

References

liquid chromatog- Paragraph 00119 raphy mass spectrometry (LCMS); electrospray ionisation (ESI); spectrum

Reaxys ID 5658209 View in Reaxys

118/204 CAS Registry Number: 61486-29-1 Chemical Name: Z(OMe)-Pyr-OSu Linear Structure Formula: C18H18N2O8 Molecular Formula: C18H18N2O8 Molecular Weight: 390.35 Type of Substance: heterocyclic InChI Key: JYPVSFUWQAVXDC-ZDUSSCGKSA-N Note:

O N

Druglikeness (1) 1 of 1

LogP

0.012

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

119.52

Lipinski Number

Veber Number

Reaxys ID 6349606 View in Reaxys

119/204 Chemical Name: ethyl (2R,3R)-N-(benzyloxycarbonyl)-3<(S)-2,2-dimethyl-1,3-dioxolan-4-yl>-5-oxopyrrolidine-2-carboxylate; ethyl (2R,3R)-N-(benzyloxycarbonyl)-3-((S)-2,2-dimethyl-1,3-dioxolan-4-yl)-5-oxopyrrolidine-2-carboxylate Linear Structure Formula: C20H25NO7 Molecular Formula: C20H25NO7 Molecular Weight: 391.421 Type of Substance: heterocyclic InChI Key: OJFMFOMKMQVGCS-ZMSDIMECSA-N Note:

O N

O O O

Substance Label (1)

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Label

References

Tatsukawa, Akira; Dan, Masashi; Ohbatake, Mika; Kawatake, Keiko; Fukata, Tomohiro; et al.; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4221 - 4227, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.145

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.26 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-11.53

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Tatsukawa, Akira; Dan, Masashi; Ohbatake, Mika; Kawatake, Keiko; Fukata, Tomohiro; et al.; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4221 - 4227, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Tatsukawa, Akira; Dan, Masashi; Ohbatake, Mika; Kawatake, Keiko; Fukata, Tomohiro; et al.; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4221 - 4227, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Tatsukawa, Akira; Dan, Masashi; Ohbatake, Mika; Kawatake, Keiko; Fukata, Tomohiro; et al.; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4221 - 4227, View in Reaxys IR Spectroscopy (1)

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1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

2986 - 698 cm**(-1)

Tatsukawa, Akira; Dan, Masashi; Ohbatake, Mika; Kawatake, Keiko; Fukata, Tomohiro; et al.; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4221 - 4227, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum; electron impact (EI)

Tatsukawa, Akira; Dan, Masashi; Ohbatake, Mika; Kawatake, Keiko; Fukata, Tomohiro; et al.; Journal of Organic Chemistry; vol. 58; nb. 16; (1993); p. 4221 - 4227, View in Reaxys

Reaxys ID 502868 View in Reaxys

120/204 CAS Registry Number: 83025-91-6 Chemical Name: 1-benzyl 2-(1,3-dioxoisoindolin-2-yl) (S)-pyrrolidine-1,2-dicarboxylate; N-Benzyloxycarbonyl-L-prolin-(N-hydroxy-phthalimid); Carbobenzoxy-L-prolin-hydroxyphthalimidester Linear Structure Formula: C21H18N2O6 Molecular Formula: C21H18N2O6 Molecular Weight: 394.384 Type of Substance: heterocyclic InChI Key: VGTDZZUUGQECRL-KRWDZBQOSA-N Note:

O N

O O

Substance Label (2) Label References SI-10

Qin, Tian; Malins, Lara R.; Edwards, Jacob T.; Merchant, Rohan R.; Novak, Alexander J. E.; Zhong, Jacob Z.; Mills, Riley B.; Yan, Ming; Yuan, Changxia; Eastgate, Martin D.; Baran, Phil S.; Angewandte Chemie - International Edition; vol. 56; nb. 1; (2017); p. 260 - 265; Angew. Chem.; vol. 129; (2017); p. 266 271,6, View in Reaxys

ZProONPht

Il'ina, A. V.; Davidovich, Yu. A.; Rogozin, S. V.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 33; (1984); p. 869 - 871; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 4; (1984); p. 943 - 945, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.717

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

101 - 102

Melting Point [°C]

109

Solvent (Melting Point)

ethanol

Nefkens,G.H.L. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 81; (1962); p. 683 - 690, View in Reaxys Chromatographic Data (1)

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Chromatographic data

Location

References

TLC (Thin layer chromatography)

supporting information

Crystal Property Description (1) Colour & Other Location Properties colourless

supporting information

References Qin, Tian; Malins, Lara R.; Edwards, Jacob T.; Merchant, Rohan R.; Novak, Alexander J. E.; Zhong, Jacob Z.; Mills, Riley B.; Yan, Ming; Yuan, Changxia; Eastgate, Martin D.; Baran, Phil S.; Angewandte Chemie - International Edition; vol. 56; nb. 1; (2017); p. 260 - 265; Angew. Chem.; vol. 129; (2017); p. 266 - 271,6, View in Reaxys

Optical Rotatory Power (3) 1 of 3

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

dichloromethane

Optical Rotatory Power [deg]

-68.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

acetic acid

Optical Rotatory Power [deg]

-82.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-81.9

Wavelength (Optical Ro- 589 tatory Power) [nm]

154/232

2017-11-12 20:29:58

Temperature (Optical Rotatory Power) [°C]

Nefkens,G.H.L. et al.; Recueil des Travaux Chimiques des Pays-Bas; vol. 81; (1962); p. 683 - 690, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

600

Location

supporting information

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

151

Location

supporting information

References

electrospray ioni- supporting inforsation (ESI); time- mation of-flight mass spectra (TOFMS); spectrum

Reaxys ID 30272339 View in Reaxys

121/204 Linear Structure Formula: C21H18N2O6 Molecular Formula: C21H18N2O6 Molecular Weight: 394.384 InChI Key: VGTDZZUUGQECRL-UHFFFAOYSA-N Note:

O O

N O

Substance Label (2) Label References 2t

Xue, Weichao; Oestreich, Martin; Angewandte Chemie - International Edition; vol. 56; nb. 38; (2017); p. 11649 - 11652; Angew. Chem.; vol. 129; (2017); p. 11808 - 11811,4, View in Reaxys

Jin, Yunhe; Yang, Haijun; Fu, Hua; Chemical Communications; vol. 52; nb. 87; (2016); p. 12909 - 12912, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.717

155/232

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H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Reaxys ID 5161653 View in Reaxys

122/204 Linear Structure Formula: C23H31NO5 Molecular Formula: C23H31NO5 Molecular Weight: 401.503 Type of Substance: heterocyclic InChI Key: KOOGUULXXJRGLT-FFLWXPKWSA-N Note:

O N

L-isomer

Substance Label (1) Label References 1i

Ohta, Tomihisa; Kimura, Toshihiko; Sato, Nobuaki; Nozoe, Shigeo; Tetrahedron Letters; vol. 29; nb. 34; (1988); p. 4303 - 4304, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.097

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 9423711 View in Reaxys

123/204 Linear Structure Formula: C21H25NO7 Molecular Formula: C21H25NO7 Molecular Weight: 403.432 Type of Substance: heterocyclic InChI Key: IUQQLYLTYKZSDM-SJRAPUSDSA-N Note:

O O O O

N O

O O

Substance Label (1) Label References 8f

Dixon, Darren J; Harding, Christopher I; Ley, Steven V; Tilbrook, D Matthew G; Chemical communications (Cambridge, England); nb. 4; (2003); p. 468 - 469, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.641

H Bond Donors

156/232

2017-11-12 20:29:58

H Bond Acceptors

Rotatable Bonds

TPSA

87.44

Lipinski Number

Veber Number

Reaxys ID 9796050 View in Reaxys

124/204 Chemical Name: benzyl (2S,3R,5R)-5-furan-3-ylmethyl-2,3-dimethoxy-2,3-dimethyl-6-oxomorpholine-4-carboxylate Linear Structure Formula: C21H25NO7 Molecular Formula: C21H25NO7 Molecular Weight: 403.432 Type of Substance: heterocyclic InChI Key: IUQQLYLTYKZSDM-UIFIKXQLSA-N Note:

O O O O

N O

O O

Substance Label (1) Label References 13g

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 7692, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.641

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

87.44

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

38 - 40

Solvent (Melting Point)

CHCl3

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 - 7692, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.45 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-15.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 - 7692, View in Reaxys NMR Spectroscopy (3)

157/232

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1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

150

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 - 7692, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

600

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 - 7692, View in Reaxys 3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy) Temperature (NMR Spectroscopy) [°C]

26.84

Frequency (NMR Spectroscopy) [MHz]

600

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 - 7692, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 - 7692, View in Reaxys

Reaxys ID 9796051 View in Reaxys

125/204 Chemical Name: benzyl (2S,3R,5S)-5-furan-3-ylmethyl-2,3-dimethoxy-2,3-dimethyl-6-oxomorpholine-4-carboxylate Linear Structure Formula: C21H25NO7 Molecular Formula: C21H25NO7 Molecular Weight: 403.432 Type of Substance: heterocyclic InChI Key: IUQQLYLTYKZSDM-WMQCIHAUSA-N

O O O O

N O

O O

158/232

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Note: Substance Label (1) Label References epi-13g

Harding, Christopher I.; Dixon, Darren J.; Ley, Steven V.; Tetrahedron; vol. 60; nb. 35; (2004); p. 7679 7692, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.641

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

87.44

Lipinski Number

Veber Number

Reaxys ID 18510783 View in Reaxys

126/204 Chemical Name: trans-4-[1-benzyloxycarbonyl-4-oxo-(2S)-pyrrolidinylmethoxy]cyclohexanecarboxylic acid ethyl ester Linear Structure Formula: C22H29NO6 Molecular Formula: C22H29NO6 Molecular Weight: 403.475 InChI Key: IWGZAQRCHFVBRS-FDYSRKEFSA-N Note:

N O

O trans trans

O trans trans O

Druglikeness (1) 1 of 1

LogP

2.26

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

82.14

Lipinski Number

Veber Number

Reaxys ID 26318804 View in Reaxys

127/204 Linear Structure Formula: C22H20N2O6 Molecular Formula: C22H20N2O6 Molecular Weight: 408.411 InChI Key: PVOCCLKXMAOCOQ-SFHVURJKSA-N Note:

O N

O O

Druglikeness (1) 1 of 1

LogP

3.106

H Bond Donors

H Bond Acceptors

Rotatable Bonds

159/232

2017-11-12 20:29:58

TPSA

93.22

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

Myeloblastin [human]

Target Synonyms

agp7; c-anca antigen; leukocyte proteinase 3; mbn; myeloblastin; neutrophil proteinase 4; np-4; p29 (myeloblastin); pr-3; pr3; prtn3; wegener autoantigen

Target Uniprot ID

p24158

Target PDB ID

1fuj

Target, Subunit, Species Myeloblastin [human] Target Mutant/Chimera Details

Myeloblastin [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Observed inhibition constant of the compound against Human proteinase 3 (PR 3)

Biological Species/NCBI Human ID

2 of 3

Substance RN

26318804View in Reaxys

Measurement Parameter

Qualitative

Unit

M-1.s-1

Measurement Object

kobs/[I]

Qualitative value

Quantitative value

300

Target Name

Cathepsin G [human]

Target Synonyms

cathepsin g; cg; ctsg

Target Uniprot ID

p08311

Target PDB ID

1au8; 1cgh; 1kyn; 1t32

Target, Subunit, Species Cathepsin G [human] Target Mutant/Chimera Details

Cathepsin G [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Observed inhibition constant of the compound against Human cathepsin G (Cat G)

Biological Species/NCBI Human ID Substance RN

26318804View in Reaxys

Measurement Parameter

Qualitative

Unit

M-1.s-1

Measurement Object

kobs/[I]

160/232

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3 of 3

Qualitative value

Quantitative value

Target Name

Neutrophil elastase [human]

Target Synonyms

bone marrow serine protease; ela2; elane; elastase-2; hle; human leukocyte elastase; medullasin; neutrophil elastase; pmn elastase

Target Uniprot ID

p08246

Target PDB ID

1b0f; 1h1b; 1hne; 1ppf; 1ppg; 2rg3; 2z7f; 3q76; 3q77; 4nzl; 4wvp

Target, Subunit, Species Neutrophil elastase [human] Target Mutant/Chimera Details

Neutrophil elastase [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Observed inhibition constant of the compound against Human leukocyte elastase (HLE)

Biological Species/NCBI Human ID Substance RN

26318804View in Reaxys

Measurement Parameter

Qualitative

Measurement Object

kobs/[I]

Reaxys ID 26318805 View in Reaxys

128/204 Linear Structure Formula: C22H20N2O6 Molecular Formula: C22H20N2O6 Molecular Weight: 408.411 InChI Key: PVOCCLKXMAOCOQ-GOSISDBHSA-N Note:

O N

O O

Druglikeness (1) 1 of 1

LogP

3.106

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Medchem (3) 1 of 3

Target Name

Myeloblastin [human]

Target Synonyms

agp7; c-anca antigen; leukocyte proteinase 3; mbn; myeloblastin; neutrophil proteinase 4; np-4; p29 (myeloblastin); pr-3; pr3; prtn3; wegener autoantigen

Target Uniprot ID

p24158

Target PDB ID

1fuj

Target, Subunit, Species Myeloblastin [human]

161/232

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Target Mutant/Chimera Details

Myeloblastin [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Observed inhibition constant of the compound against Human proteinase 3 (PR 3)

Biological Species/NCBI Human ID

2 of 3

Substance RN

26318805View in Reaxys

Measurement Parameter

Qualitative

Unit

M-1.s-1

Measurement Object

kobs/[I]

Qualitative value

Quantitative value

190

Target Name

Cathepsin G [human]

Target Synonyms

cathepsin g; cg; ctsg

Target Uniprot ID

p08311

Target PDB ID

1au8; 1cgh; 1kyn; 1t32

Target, Subunit, Species Cathepsin G [human] Target Mutant/Chimera Details

Cathepsin G [human]:Wild

Target Species (Bioactivity)

human

Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Observed inhibition constant of the compound against Human cathepsin G (Cat G)

Biological Species/NCBI Human ID

3 of 3

Substance RN

26318805View in Reaxys

Qualitative Results

IA = in active

Measurement Parameter

Qualitative

Measurement Object

kobs/[I]

Target Name

Neutrophil elastase [human]

Target Synonyms

bone marrow serine protease; ela2; elane; elastase-2; hle; human leukocyte elastase; medullasin; neutrophil elastase; pmn elastase

Target Uniprot ID

p08246

Target PDB ID

1b0f; 1h1b; 1hne; 1ppf; 1ppg; 2rg3; 2z7f; 3q76; 3q77; 4nzl; 4wvp

Target, Subunit, Species Neutrophil elastase [human] Target Mutant/Chimera Details

Neutrophil elastase [human]:Wild

Target Species (Bioactivity)

human

162/232

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Substance Action on Target

Inhibitor

Bioassay Category

In Vitro (Efficacy)

Bioassay Details

Observed inhibition constant of the compound against Human leukocyte elastase (HLE)

Biological Species/NCBI Human ID Substance RN

26318805View in Reaxys

Measurement Parameter

Qualitative

Measurement Object

kobs/[I]

Reaxys ID 5360470 View in Reaxys

129/204 CAS Registry Number: 138858-46-5 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α(phenylmethyl)pyroglutamate Linear Structure Formula: C24H27NO5 Molecular Formula: C24H27NO5 Molecular Weight: 409.482 Type of Substance: heterocyclic InChI Key: PGCSHTYHAOMAAB-UXHICEINSA-N Note:

O N O

O O

Substance Label (1) Label References 8a

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.425

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

112 - 114

Solvent (Melting Point)

ethyl acetate; hexane

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.75 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-59.2

Wavelength (Optical Ro- 589 tatory Power) [nm]

163/232

2017-11-12 20:29:58

Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

1792 - 1740 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5666590 View in Reaxys

130/204 CAS Registry Number: 53666-00-5 Chemical Name: Z-Pro-ONB Linear Structure Formula: C22H22N2O6 Molecular Formula: C22H22N2O6 Molecular Weight: 410.426 Type of Substance: heterocyclic InChI Key: VDFJLKLCXAQMFG-HNICDYJYSA-N Note:

O O O O

N O

Substance Label (1) Label References 3 (Z-Prolin)

Henklein, Peter; Ott, Tilmann; Jaehrling, Renate; Scharfenberg, Peter; Heyne, Hans-Ulrich; Niedrich, Hartmut; Zeitschrift fuer Chemie (Stuttgart, Germany); vol. 29; nb. 8; (1989); p. 289 - 290, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.722

H Bond Donors

164/232

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H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Reaxys ID 5386034 View in Reaxys

131/204 CAS Registry Number: 138858-35-2 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxy-2-furylmethyl)pyroglutamate Linear Structure Formula: C22H25NO7 Molecular Formula: C22H25NO7 Molecular Weight: 415.443 Type of Substance: heterocyclic InChI Key: YRCPPLLDYKAAPF-MZQXSQAVSA-N Note:

O N

O OH O

Substance Label (1) Label References 2g

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.787

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

106.28

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-2.94

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

165/232

2017-11-12 20:29:58

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3540 - 1740 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5386035 View in Reaxys

132/204 CAS Registry Number: 138858-35-2 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxy-2-furylmethyl)pyroglutamate Linear Structure Formula: C22H25NO7 Molecular Formula: C22H25NO7 Molecular Weight: 415.443 Type of Substance: heterocyclic InChI Key: YRCPPLLDYKAAPF-LNKXUWQBSA-N Note:

O N

O OH O

Substance Label (1) Label References 3g

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

2.787

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

106.28

Lipinski Number

Veber Number

166/232

2017-11-12 20:29:58

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2.1 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

1.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3400 - 1740 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 18508807 View in Reaxys

133/204

167/232

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O N O

Linear Structure Formula: C21H26N2O7 Molecular Formula: C21H26N2O7 Molecular Weight: 418.447 InChI Key: XCWGGEYCFNXCPP-NRFANRHFSA-N Note:

O O

O N

O O

Druglikeness (1) 1 of 1

LogP

1.689

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.45

Lipinski Number

Veber Number

Reaxys ID 950887 View in Reaxys

O O N O

134/204 CAS Registry Number: 49761-37-7; 63861-48-3 Chemical Name: 2-(1-benzyloxycarbonyl-5-oxo-prolyloxy)-3a, 4,7,7a-tetrahydro-4,7-methano-isoindole-1,3-dione Linear Structure Formula: C22H20N2O7 Molecular Formula: C22H20N2O7 Molecular Weight: 424.41 Type of Substance: heterocyclic InChI Key: GCCHPCDCRIQBDR-UHFFFAOYSA-N Note:

O O

Druglikeness (1) 1 of 1

LogP

1.064

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

110.29

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

145 - 146

Patent; Abbott; DE2406543; (1974); Chem.Abstr.; vol. 87; nb. 39849, View in Reaxys

Reaxys ID 5167262 View in Reaxys

135/204

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CAS Registry Number: 127949-78-4 Chemical Name: t-butyl (2S)-1-benzyloxycarbonyl-4-(hydroxyphenylmethyl)pyroglutamate Linear Structure Formula: C24H27NO6 Molecular Formula: C24H27NO6 Molecular Weight: 425.481 Type of Substance: heterocyclic InChI Key: YBGGMSDQVWSFLR-GPJFCIFZSA-N Note:

HO O N O

O O

Substance Label (1) Label References 2a

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.09

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.5 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-11.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

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3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3490 - 1735 cm**(-1)

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Reaxys ID 5385823 View in Reaxys

136/204 CAS Registry Number: 127949-78-4 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxyphenylmethyl)pyroglutamate Linear Structure Formula: C24H27NO6 Molecular Formula: C24H27NO6 Molecular Weight: 425.481 Type of Substance: heterocyclic InChI Key: YBGGMSDQVWSFLR-NFBCFJMWSA-N Note:

HO O N O

O O

Substance Label (1) Label References 2c

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.09

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

115 - 117

Solvent (Melting Point)

ethyl acetate; hexane

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.6 g/100ml

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Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-17.24

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3500 - 1758 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5385824 View in Reaxys

137/204

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CAS Registry Number: 127949-78-4 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxyphenylmethyl)pyroglutamate Linear Structure Formula: C24H27NO6 Molecular Formula: C24H27NO6 Molecular Weight: 425.481 Type of Substance: heterocyclic InChI Key: YBGGMSDQVWSFLR-LFPSWIHMSA-N Note:

HO O N O

O O

Substance Label (1) Label References 3c

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.09

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

97 - 101

Solvent (Melting Point)

ethyl acetate; hexane

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.95 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

1.55

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy)

172/232

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Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 4 of 4

Description (NMR Spec- NOE troscopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3550 - 1775 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 6024308 View in Reaxys

138/204

CAS Registry Number: 113332-48-2 Chemical Name: Z-Hyp-ONB Linear Structure Formula: C22H22N2O7 Molecular Formula: C22H22N2O7 Molecular Weight: 426.426 Type of Substance: heterocyclic InChI Key: FJZSQEQHISDWAK-SYRBXRPPSA-N Note:

Druglikeness (1) 1 of 1

LogP

0.692

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

113.45

Lipinski Number

173/232

2017-11-12 20:29:58

Veber Number

Reaxys ID 7731151 View in Reaxys

139/204 Linear Structure Formula: C23H24DNO7 Molecular Formula: C23H25NO7 Molecular Weight: 428.446 Type of Substance: heterocyclic InChI Key: DJCHSBXXRFYOEW-ZKJKMRBOSA-N Note:

O O N

O O

Druglikeness (1) 1 of 1

LogP

2.761

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

NMR Spectroscopy (4) 1 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Bowler, Andrew N.; Dinsmore, Andrew; Doyle, Paul M.; Young, Douglas W.; Journal of the Chemical Society Perkin Transactions 1; nb. 9; (1997); p. 1297 - 1306, View in Reaxys 2 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Bowler, Andrew N.; Dinsmore, Andrew; Doyle, Paul M.; Young, Douglas W.; Journal of the Chemical Society Perkin Transactions 1; nb. 9; (1997); p. 1297 - 1306, View in Reaxys 3 of 4

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Bowler, Andrew N.; Dinsmore, Andrew; Doyle, Paul M.; Young, Douglas W.; Journal of the Chemical Society Perkin Transactions 1; nb. 9; (1997); p. 1297 - 1306, View in Reaxys 4 of 4

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Bowler, Andrew N.; Dinsmore, Andrew; Doyle, Paul M.; Young, Douglas W.; Journal of the Chemical Society Perkin Transactions 1; nb. 9; (1997); p. 1297 - 1306, View in Reaxys IR Spectroscopy (1)

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1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

1796 - 1730 cm**(-1)

Bowler, Andrew N.; Dinsmore, Andrew; Doyle, Paul M.; Young, Douglas W.; Journal of the Chemical Society Perkin Transactions 1; nb. 9; (1997); p. 1297 - 1306, View in Reaxys

Reaxys ID 6019846 View in Reaxys

O O

140/204 CAS Registry Number: 98807-05-7 Chemical Name: Z-Pro-OCamp Linear Structure Formula: C23H28N2O6 Molecular Formula: C23H28N2O6 Molecular Weight: 428.485 Type of Substance: heterocyclic InChI Key: SXJPFPWORVUXBW-HFNFZTFUSA-N Note:

N H O

O O

Druglikeness (1) 1 of 1

LogP

2.674

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

ethanol

Optical Rotatory Power [deg]

-29.8

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Takeda, Kazuyoshi; Tsuboyama, Kanoko; Suzuki, Akira; Ogura, Haruo; Chemical and Pharmaceutical Bulletin; vol. 33; (1985); p. 2545 - 2548, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1810 - 1715 cm**(-1)

Takeda, Kazuyoshi; Tsuboyama, Kanoko; Suzuki, Akira; Ogura, Haruo; Chemical and Pharmaceutical Bulletin; vol. 33; (1985); p. 2545 - 2548, View in Reaxys

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Reaxys ID 21247650 View in Reaxys

O O N

141/204 CAS Registry Number: 1280225-77-5 Linear Structure Formula: C23H28N2O6 Molecular Formula: C23H28N2O6 Molecular Weight: 428.485 InChI Key: AJJIEPKPDXDEHS-SFHVURJKSA-N Note:

N O

Druglikeness (1) 1 of 1

LogP

3.594

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.22

Lipinski Number

Veber Number

Reaxys ID 5782872 View in Reaxys

142/204 CAS Registry Number: 78685-16-2 Chemical Name: Z-D-pGlu-OPfp; Benzyloxycarbonyl-D-pyroglutamic acid pentafluorophenyl ester Linear Structure Formula: C19H12F5NO5 Molecular Formula: C19H12F5NO5 Molecular Weight: 429.3 Type of Substance: heterocyclic InChI Key: GXRIHBFYWAYOGB-SNVBAGLBSA-N Note:

F F

H OO

N O O

Druglikeness (1) 1 of 1

LogP

3.758

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

81 - 82

Szirtes, Tamas; Kisfaludy, Lajos; Palosi, Eva; Szporny, Laszlo; Journal of Medicinal Chemistry; vol. 27; nb. 6; (1984); p. 741 - 745, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

acetic acid

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Optical Rotatory Power [deg]

40.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Szirtes, Tamas; Kisfaludy, Lajos; Palosi, Eva; Szporny, Laszlo; Journal of Medicinal Chemistry; vol. 27; nb. 6; (1984); p. 741 - 745, View in Reaxys

Reaxys ID 5782873 View in Reaxys

143/204 CAS Registry Number: 78148-14-8 Chemical Name: benzyloxycarbonylpyroglutamic acid pentafluorophenyl ester; pentafluorophenyl N-benzyloxycarbonylpyroglutamate; Z-pGlu-OPfp Linear Structure Formula: C19H12F5NO5 Molecular Formula: C19H12F5NO5 Molecular Weight: 429.3 Type of Substance: heterocyclic InChI Key: GXRIHBFYWAYOGB-JTQLQIEISA-N Note:

F F

H OO

N O O

Substance Label (1) Label References Z-pGluOPFP

Liang, Bo; Vera, Matthew D.; Joullie, Madeleine M.; Journal of Organic Chemistry; vol. 65; nb. 15; (2000); p. 4762 - 4765, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.758

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

80 - 82

Szirtes, Tamas; Kisfaludy, Lajos; Palosi, Eva; Szporny, Laszlo; Journal of Medicinal Chemistry; vol. 27; nb. 6; (1984); p. 741 - 745, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

acetic acid

Optical Rotatory Power [deg]

-40.4

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

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Szirtes, Tamas; Kisfaludy, Lajos; Palosi, Eva; Szporny, Laszlo; Journal of Medicinal Chemistry; vol. 27; nb. 6; (1984); p. 741 - 745, View in Reaxys

Reaxys ID 8508134 View in Reaxys O

Chemical Name: diphenylmethyl N-carbobenzyloxypyroglutamate Linear Structure Formula: C26H23NO5 Molecular Formula: C26H23NO5 Molecular Weight: 429.472 Type of Substance: heterocyclic InChI Key: NCQJHJZXPCYELM-UHFFFAOYSA-N Note:

N O

144/204

Substance Label (1) Label References 10

Akasaka, Kozo; Akamatsu, Hiroshi; Kimoto, Yuichi; Komatsu, Yuki; Shimizu, Toshikazu; Shimomura, Naoyuki; Tagami, Katsuya; Negi, Shigeto; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 11; (1999); p. 1525 - 1531, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.672

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

169 - 170

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Akasaka, Kozo; Akamatsu, Hiroshi; Kimoto, Yuichi; Komatsu, Yuki; Shimizu, Toshikazu; Shimomura, Naoyuki; Tagami, Katsuya; Negi, Shigeto; Chemical and Pharmaceutical Bulletin; vol. 47; nb. 11; (1999); p. 1525 - 1531, View in Reaxys 2 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Description (NMR Spec- Chemical shifts troscopy)

178/232

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Nucleus (NMR Spectroscopy)

13C

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Reaxys ID 26551388 View in Reaxys

Chemical Name: (2R)-1-benzyl 2-methyl 5-oxo-4-((2,2,6,6-tetramethylpiperidin-1-yl)oxy)pyrrolidine-1,2-dicarboxylate Linear Structure Formula: C23H32N2O6 Molecular Formula: C23H32N2O6 Molecular Weight: 432.517 InChI Key: PTOMUXUJZKEYBI-QNSVNVJESA-N Note:

O O

145/204

O N

O O

Substance Label (1) Label References 5k

Drouet, Fleur; Zhu, Jieping; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 18; (2013); p. 3563 - 3569, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.51

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

85.38

Lipinski Number

Veber Number

Melting Point (2) 1 of 2

Melting Point [°C]

34 - 36

Location

supporting information

Drouet, Fleur; Zhu, Jieping; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 18; (2013); p. 3563 - 3569, View in Reaxys 2 of 2

Melting Point [°C]

87 - 89

Location

supporting information

Drouet, Fleur; Zhu, Jieping; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 18; (2013); p. 3563 - 3569, View in Reaxys Crystal Property Description (1) Colour & Other Location Properties

References

179/232

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white

supporting information

Drouet, Fleur; Zhu, Jieping; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 18; (2013); p. 3563 - 3569, View in Reaxys

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Location

supporting information

Drouet, Fleur; Zhu, Jieping; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 18; (2013); p. 3563 - 3569, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Location

supporting information

Drouet, Fleur; Zhu, Jieping; Masson, Geraldine; Advanced Synthesis and Catalysis; vol. 355; nb. 18; (2013); p. 3563 - 3569, View in Reaxys

Reaxys ID 14104438 View in Reaxys

146/204 CAS Registry Number: 437760-93-5 Chemical Name: 1-benzyl 2-tert-butyl (2S,4R)-5-oxo-4-[(2E)-3phenyl-2-propenyl]-1,2-pyrrolidinedicarboxylate Linear Structure Formula: C26H29NO5 Molecular Formula: C26H29NO5 Molecular Weight: 435.52 InChI Key: YMFQXRWQPIPNEW-VNHPBQPXSA-N Note:

O O

N O

Druglikeness (1) 1 of 1

LogP

5.449

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy)

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Frequency (NMR Spectroscopy) [MHz]

300

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

Signals [ppm]

7.22 - 7.43; 6.46; 6.06 - 6.18; 5.2 - 5.33; 4.5; 2.63 - 2.88; 2.33 - 2.45; 2.12 - 2.24; 1.38

Kind of signal

m, 10H; d, J=15.7, 1H; m, 1H; m, 2H; dd, J=9.3, 1.7, 1H; m, 1H; m, 1H; m, 2H; s, 9H

NMR (300 MHz, CDCl3) δ7.43-7.22 (m, 10H), 6.46 (d, J=15.7, 1H), 6.18-6.06 (m, 1H), 5.33-5.20 (m, 2H), 4.50 (dd, J=9.3, 1.7, 1H), 2.88-2.63 (m, 1H), 2.45-2.33 (m, 1H), 2.24-2.12 (m, 2H), 1.38 (s, 9H)

Patent; Glunz, Peter William; Douty, Brent Dale; Han, Wei; US2003/64962; (2003); (A1) English, View in Reaxys Mass Spectrometry (1) Comment (Mass Peak Spectrometry) Molecular peak

References

436.2 m/z

Patent; Glunz, Peter William; Douty, Brent Dale; Han, Wei; US2003/64962; (2003); (A1) English, View in Reaxys

Reaxys ID 19895832 View in Reaxys

147/204 CAS Registry Number: 1265173-12-3 Linear Structure Formula: C25H27NO6 Molecular Formula: C25H27NO6 Molecular Weight: 437.492 InChI Key: HFJPTIFUTBIXHW-TUSQITKMSA-N Note:

O N

O OH O

Druglikeness (1) 1 of 1

LogP

3.512

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties yellow

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.95 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

chloroform

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Optical Rotatory Power [deg]

1.5

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) ESI (Electrospray Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An ionisation); HRMS Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys (High resolution mass spectrometry); LCMS (Liquid chromatography mass spectrometry); Spectrum

Reaxys ID 9807831 View in Reaxys

148/204

182/232

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CAS Registry Number: 1026642-81-8 Linear Structure Formula: HCOCH2CHNCO2CH2C6H5CH2CHCCH2CH3CH2OCH2C6H4OC H3CH Molecular Formula: C26H31NO5 Molecular Weight: 437.536 Type of Substance: heterocyclic InChI Key: JXUVCFJIUVRWQU-RGVLZGJSSA-N Note:

O N

Substance Label (1) Label References 14

Chavan, Subhash P.; Sivappa, Rasapalli; Tetrahedron Letters; vol. 45; nb. 20; (2004); p. 3941 - 3943, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.611

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

65.07

Lipinski Number

Veber Number

Reaxys ID 502928 View in Reaxys

149/204

CAS Registry Number: 3303-64-8 Chemical Name: N-Benzyloxycarbonyl-L-pyroglutaminsaeure(2,4,5-trichlor-phenylester) Linear Structure Formula: C19H14Cl3NO5 Molecular Formula: C19H14Cl3NO5 Molecular Weight: 442.683 Type of Substance: heterocyclic InChI Key: FYEXIHDBKJSWRV-UHFFFAOYSA-N Note:

O Cl

Druglikeness (1) 1 of 1

LogP

4.819

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 502929 View in Reaxys

150/204

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CAS Registry Number: 5910-46-3 Chemical Name: Z-Pyr-OTCP Linear Structure Formula: C19H14Cl3NO5 Molecular Formula: C19H14Cl3NO5 Molecular Weight: 442.683 Type of Substance: heterocyclic InChI Key: FYEXIHDBKJSWRV-HNNXBMFYSA-N Note:

Cl Cl O H

Cl OO N O O

Druglikeness (1) 1 of 1

LogP

4.819

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

162 - 163

Patent; ICI; BE665591; (1964); Chem.Abstr.; vol. 64; nb. 19774b; (1966), View in Reaxys

Reaxys ID 5386185 View in Reaxys

151/204 CAS Registry Number: 138858-33-0 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxy(p-fluoroohenyl)methyl)pyroglutamate; tert-butyl (2S)-1(benzyloxycarbonyl)-4α-[hydroxy(p-fluoroohenyl)methyl]pyroglutamate Linear Structure Formula: C24H26FNO6 Molecular Formula: C24H26FNO6 Molecular Weight: 443.472 Type of Substance: heterocyclic InChI Key: PTEWQUOUZRHSSO-NFBCFJMWSA-N Note:

F HO O N O

O O

Substance Label (1) Label References 2e

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.251

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

102 - 106

Solvent (Melting Point)

ethyl acetate; hexane

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Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.35 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-7.58

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3500 - 1750 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5386186 View in Reaxys

152/204

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CAS Registry Number: 138858-33-0 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxy(p-fluoroohenyl)methyl)pyroglutamate; tert-butyl (2S)-1(benzyloxycarbonyl)-4β-[hydroxy(p-fluoroohenyl)methyl]pyroglutamate Linear Structure Formula: C24H26FNO6 Molecular Formula: C24H26FNO6 Molecular Weight: 443.472 Type of Substance: heterocyclic InChI Key: PTEWQUOUZRHSSO-LFPSWIHMSA-N Note:

F HO O N O

O O

Substance Label (1) Label References 3e

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.251

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.55 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

3.77

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy)

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Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3500 - 1750 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 8509807 View in Reaxys

153/204 Chemical Name: diphenylmethyl cis-N-benzyloxycarbonyl-4methylpyroglutamate Linear Structure Formula: C27H25NO5 Molecular Formula: C27H25NO5 Molecular Weight: 443.499 Type of Substance: heterocyclic InChI Key: JIVDSLDCMKIKPG-AUSIDOKSSA-N Note:

O N

racemate

Substance Label (1) Label References cis-11

Druglikeness (1) 1 of 1

LogP

4.965

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

109

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Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

Reaxys ID 8509808 View in Reaxys

154/204 Chemical Name: diphenylmethyl trans-N-benzyloxycarbonyl-4methylpyroglutamate Linear Structure Formula: C27H25NO5 Molecular Formula: C27H25NO5 Molecular Weight: 443.499 Type of Substance: heterocyclic InChI Key: JIVDSLDCMKIKPG-WMZHIEFXSA-N Note:

O N

racemate

Substance Label (1) Label References

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trans-11

Druglikeness (1) 1 of 1

LogP

4.965

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

108

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

nujol

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Reaxys ID 4087601 View in Reaxys

155/204 CAS Registry Number: 101611-38-5 Linear Structure Formula: C13H13NO5*C12H23N Molecular Formula: C12H23N*C13H13NO5 Molecular Weight: 444.571 Type of Substance: heterocyclic InChI Key: YZBYZSRZSLSPSI-UHFFFAOYSA-N Note:

H N

O N

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

95.94

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

193 - 196

Voelter et al.; Chemiker-Zeitung; vol. 102; (1978); p. 109, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Optical Rotatory Power [deg]

-15.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Voelter et al.; Chemiker-Zeitung; vol. 102; (1978); p. 109, View in Reaxys

Reaxys ID 5213061 View in Reaxys

156/204 CAS Registry Number: 38596-35-9 Chemical Name: dicyclohexylamine salt of N-benzyloxycarbonyl-(L)-pyroglutamic acid Linear Structure Formula: C13H13NO5*C12H23N Molecular Formula: C12H23N*C13H13NO5 Molecular Weight: 444.571 Type of Substance: heterocyclic InChI Key: YZBYZSRZSLSPSI-PPHPATTJSA-N Note:

H N

O O HO

O N

Substance Label (1) Label References Z-L-pGlu*DCHA

Matsuda, Fuyuhiko; Itoh, Shin; Hattori, Noritaka; Yanagiya, Mitsutoshi; Matsumoto, Takeshi; Tetrahedron; vol. 41; nb. 18; (1985); p. 3625 - 3631, View in Reaxys

Druglikeness (1) 1 of 1

H Bond Donors

H Bond Acceptors

190/232

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Rotatable Bonds

TPSA

95.94

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

208

Patent; S. A. Panmedica; US4661512; (1987); (A1) English, View in Reaxys

Reaxys ID 8938493 View in Reaxys

157/204 CAS Registry Number: 359882-13-6 Chemical Name: 1-benzyloxycarbonyl-2-[(2-bromophenyl)methyl]-2-methoxycarbonyl-4-oxopyrrolidine Linear Structure Formula: C21H20BrNO5 Molecular Formula: C21H20BrNO5 Molecular Weight: 446.298 Type of Substance: heterocyclic InChI Key: AGFKSIDSZBDPAG-OAQYLSRUSA-N Note:

O O O

Substance Label (2) Label References 14

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys

Tamura; Yanagimachi; Kobayashi; Ishibashi; Organic letters; vol. 3; nb. 16; (2001); p. 2427 - 2429, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.159

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

270

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

191/232

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Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

270

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys

Reaxys ID 9583273 View in Reaxys

158/204 Chemical Name: 1-benzyloxycarbonyl-2-[(2-bromophenyl)methyl]-2-methoxycarbonyl-4-oxopyrrolidine Linear Structure Formula: C21H20BrNO5 Molecular Formula: C21H20BrNO5 Molecular Weight: 446.298 Type of Substance: heterocyclic InChI Key: AGFKSIDSZBDPAG-NRFANRHFSA-N Note:

O O O

Substance Label (1) Label References enantiomer of 14

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.159

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 15050642 View in Reaxys

159/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy(phenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C25H25NO7 Molecular Formula: C25H25NO7 Molecular Weight: 451.476 InChI Key: NSFMRQQZQDUGBN-BVVFMGSASA-N Note:

O O O O O O

N O

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Druglikeness (1) 1 of 1

LogP

3.966

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Reaxys ID 14454758 View in Reaxys

160/204 CAS Registry Number: 191851-62-4 Chemical Name: N-(benzyloxycarbonyl)-cis-4'-(benzyloxy)-Lproline succinate ester Linear Structure Formula: C24H24N2O7 Molecular Formula: C24H24N2O7 Molecular Weight: 452.464 InChI Key: ZFPCWRPBQIELSB-PMACEKPBSA-N Note:

O N

O O O

N O

Substance Label (1) Label References 1055A

Patent; The Scripps Research Institute; US6900238; (2005); (B1) English, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.954

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.45

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties white

Patent; The Scripps Research Institute; US6900238; (2005); (B1) English, View in Reaxys

NMR Spectroscopy (1) 1 of 1

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (CDCl3, 400 MHz) (two distinct rotamers, only major rotamer noted here) d 7.38-7.25 (10H, m), 5.23 (1H, d, J=12.4 Hz, ab-Cbz), 5.10 (1H, d, 12.4 Hz ab-Cbz), 4.75 (1H, dd, J=9.4, 3.0 Hz, a-H), 4.63 (1H, d J=12.5 Hz, ab-Bn), 4.48 (1H, d, J=12.5 Hz, abBn), 4.15-4.09 (1H, m, CH-OBn), 3.75-3.62 (2H, m, NCH2CHOBn), 2.82 (4H, s, succ.CH2), 2.65-2.62 (1H, m, NCH2CHOBnCH2), 2.47-2.34 (1H, m, NCH2CHOBnCH2)

Patent; The Scripps Research Institute; US6900238; (2005); (B1) English, View in Reaxys

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Reaxys ID 19895835 View in Reaxys

Linear Structure Formula: C25H27NO7 Molecular Formula: C25H27NO7 Molecular Weight: 453.492 InChI Key: WNYQMPVBQUFODG-OPXMRZJTSA-N Note:

O O

161/204

OH OH O

Druglikeness (1) 1 of 1

LogP

3.098

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

113.37

Lipinski Number

Veber Number

Reaxys ID 3636580 View in Reaxys O

162/204 CAS Registry Number: 127420-02-4 Chemical Name: (3R,5R,6S)-4-(Benzyloxycarbonyl)-5,6-diphenyl-3-(2'-furyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one Linear Structure Formula: C28H23NO5 Molecular Formula: C28H23NO5 Molecular Weight: 453.494 Type of Substance: heterocyclic InChI Key: PGDJEEPGYJVRGS-CYXNTTPDSA-N Note:

O O

N O

Substance Label (1) Label References 7

Williams; Hendrix; Journal of Organic Chemistry; vol. 55; nb. 12; (1990); p. 3723 - 3727, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.124

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.98

Lipinski Number

Veber Number

Reaxys ID 6017842 View in Reaxys

163/204

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CAS Registry Number: 112741-67-0 Chemical Name: (3S,5S,6R)-4-(benzyloxycarbonyl)-3-(2'-furanyl)-5,6-diphenyl-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one Linear Structure Formula: C28H23NO5 Molecular Formula: C28H23NO5 Molecular Weight: 453.494 Type of Substance: heterocyclic InChI Key: PGDJEEPGYJVRGS-KKUQBAQOSA-N Note:

O O

N O

Substance Label (1) Label References 21

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.124

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.98

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

203 - 204

Solvent (Melting Point)

hexane; ethyl acetate

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.26 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

19.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

119.9

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys

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2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

119.9

Comment (NMR Spectroscopy)

1H-1H.

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

1755 - 1210 cm**(-1)

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys

Reaxys ID 6028746 View in Reaxys O

O O

O H O

164/204 Linear Structure Formula: C23H22N2O8 Molecular Formula: C23H22N2O8 Molecular Weight: 454.436 Type of Substance: heterocyclic InChI Key: FFYKJQMVFYXXEQ-HNICDYJYSA-N Note:

O O

Substance Label (1) Label References 2 (Z-Prolin)

Druglikeness (1) 1 of 1

LogP

2.343

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

119.52

Lipinski Number

Veber Number

Reaxys ID 5386356 View in Reaxys

165/204

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CAS Registry Number: 138858-32-9 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxy(p-methoxyphenyl)methyl)pyroglutamate; tert-butyl (2S)-1(benzyloxycarbonyl)-4α-[hydroxy(p-methoxyphenyl)methyl]pyroglutamate Linear Structure Formula: C25H29NO7 Molecular Formula: C25H29NO7 Molecular Weight: 455.508 Type of Substance: heterocyclic InChI Key: FXIWAHQVBJTUFN-AHTKWCMKSA-N Note:

O HO O N O

O O

Substance Label (1) Label References 2d

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.005

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.37

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

125 - 126

Solvent (Melting Point)

ethyl acetate; hexane

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-11.16

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys

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2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3550 - 1756 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5386357 View in Reaxys

166/204 CAS Registry Number: 138858-32-9 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxy(p-methoxyphenyl)methyl)pyroglutamate; tert-butyl (2S)-1(benzyloxycarbonyl)-4β-[hydroxy(p-methoxyphenyl)methyl]pyroglutamate Linear Structure Formula: C25H29NO7 Molecular Formula: C25H29NO7 Molecular Weight: 455.508 Type of Substance: heterocyclic InChI Key: FXIWAHQVBJTUFN-PDYHCXRVSA-N Note:

O HO O N O

O O

Substance Label (1) Label References 3d

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.005

H Bond Donors

H Bond Acceptors

Rotatable Bonds

198/232

2017-11-12 20:29:58

TPSA

102.37

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

2.86

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3500 - 1745 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1)

199/232

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Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5386521 View in Reaxys

167/204 CAS Registry Number: 138858-36-3 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxy(m-methoxyphenyl)methyl)pyroglutamate; tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-[hydroxy(m-methoxyphenyl)methyl]pyroglutamate Linear Structure Formula: C25H29NO7 Molecular Formula: C25H29NO7 Molecular Weight: 455.508 Type of Substance: heterocyclic InChI Key: MTXKIDFRXCLUDQ-AHTKWCMKSA-N Note:

HO O N O

O O

Substance Label (1) Label References 2h

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.005

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.37

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

200/232

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Comment (IR Spectroscopy)

3500 - 1745 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5386522 View in Reaxys

168/204 CAS Registry Number: 138858-36-3 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxy(m-methoxyphenyl)methyl)pyroglutamate; tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-[hydroxy(m-methoxyphenyl)methyl]pyroglutamate Linear Structure Formula: C25H29NO7 Molecular Formula: C25H29NO7 Molecular Weight: 455.508 Type of Substance: heterocyclic InChI Key: MTXKIDFRXCLUDQ-PDYHCXRVSA-N Note:

HO O N O

O O

Substance Label (1) Label References 3h

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.005

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.37

Lipinski Number

Veber Number

NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1)

201/232

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1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

Comment (IR Spectroscopy)

3500 - 1750 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5191668 View in Reaxys

169/204 CAS Registry Number: 95863-95-9 Linear Structure Formula: C23H24N2O8 Molecular Formula: C23H24N2O8 Molecular Weight: 456.452 Type of Substance: heterocyclic InChI Key: AAKWRUGMBJZELU-DMZRMEPZSA-N Note:

O N

O O

Substance Label (1) Label References Fig. 3.

Shinagawa, Susumu; Kasahara, Fumiko; Wada, Yoshikazu; Harada, Setsuo; Asai, Mitsuko; Tetrahedron; vol. 40; nb. 18; (1984); p. 3465 - 3470, View in Reaxys

Druglikeness (1) 1 of 1

LogP

0.449

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

133.68

Lipinski Number

Veber Number

Reaxys ID 5174417 View in Reaxys

170/204 CAS Registry Number: 127949-80-8 Chemical Name: benzyl (2S)-1-benzyloxycarbonyl-4-(hydroxyphenylmethyl)pyroglutamate Linear Structure Formula: C27H25NO6 Molecular Formula: C27H25NO6 Molecular Weight: 459.499 Type of Substance: heterocyclic InChI Key: PBCDGEUCSANAJF-WLXPTCNVSA-N Note:

O N

O OH

202/232

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Substance Label (1) Label References 2c

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.5

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.5 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-2.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

203/232

2017-11-12 20:29:58

IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3470 - 1745 cm**(-1)

Baldwin, Jack E.; Miranda, Tania; Moloney, Mark; Hokelek, Tuncer; Tetrahedron; vol. 45; nb. 23; (1989); p. 7459 - 7468, View in Reaxys

Reaxys ID 5386187 View in Reaxys

171/204 CAS Registry Number: 138858-34-1 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4α-(hydroxy(p-chlorophenyl)methyl)pyroglutamate; tert-butyl (2S)-1(benzyloxycarbonyl)-4α-[hydroxy(p-chlorophenyl)methyl]pyroglutamate Linear Structure Formula: C24H26ClNO6 Molecular Formula: C24H26ClNO6 Molecular Weight: 459.927 Type of Substance: heterocyclic InChI Key: HZRPXMXMEQYHCS-NFBCFJMWSA-N Note:

Cl HO O N O

O O

Substance Label (1) Label References 2f

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.712

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

119 - 125

Solvent (Melting Point)

ethyl acetate; hexane

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.45 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

-5.68

Wavelength (Optical Ro- 589 tatory Power) [nm]

204/232

2017-11-12 20:29:58

Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Comment (IR Spectroscopy)

3500 - 1752 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 5386188 View in Reaxys

172/204 CAS Registry Number: 138858-34-1 Chemical Name: tert-butyl (2S)-1-(benzyloxycarbonyl)-4β-(hydroxy(p-chlorophenyl)methyl)pyroglutamate; tert-butyl (2S)-1(benzyloxycarbonyl)-4β-[hydroxy(p-chlorophenyl)methyl]pyroglutamate Linear Structure Formula: C24H26ClNO6 Molecular Formula: C24H26ClNO6 Molecular Weight: 459.927 Type of Substance: heterocyclic InChI Key: HZRPXMXMEQYHCS-LFPSWIHMSA-N Note:

Cl HO O N O

O O

Substance Label (1) Label References 3f

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Druglikeness (1)

205/232

2017-11-12 20:29:58

1 of 1

LogP

4.712

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

93.14

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.4 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

1.39

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys NMR Spectroscopy (3) 1 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- CDCl3 scopy) Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys 3 of 3

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- CDCl3 scopy) Comment (NMR Spectroscopy)

1H-1H

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

neat (no solvent)

206/232

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Comment (IR Spectroscopy)

3500 - 1750 cm**(-1)

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 - 1924, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Dikshit, Dinesh K.; Panday, Sharad K.; Journal of Organic Chemistry; vol. 57; nb. 6; (1992); p. 1920 1924, View in Reaxys

Reaxys ID 15050795 View in Reaxys

173/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy-(2methylphenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C26H27NO7 Molecular Formula: C26H27NO7 Molecular Weight: 465.503 InChI Key: XDHPZUSTSKKNPK-XOYNAWAESA-N Note:

O O O O O O

N O

Druglikeness (1) 1 of 1

LogP

4.403

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Reaxys ID 19895836 View in Reaxys

CAS Registry Number: 1196704-25-2 Chemical Name: 1-benzyl 2-methyl (2R,3S,4R)-4-[2-(benzyloxy)ethyl]-3-hydroxy-3-methyl-5-oxo-2-vinylpyrrolidine-1,2-dicarboxylate Linear Structure Formula: C26H29NO7 Molecular Formula: C26H29NO7 Molecular Weight: 467.519 InChI Key: GMEYUWPDAGCYFW-MZBJOSPHSA-N Note:

O O

174/204

O OH O

Druglikeness (1) 1 of 1

LogP

3.419

H Bond Donors

H Bond Acceptors

Rotatable Bonds

207/232

2017-11-12 20:29:58

TPSA

102.37

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colourless

Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun-Ichi; Sato, Takaaki; Chida, Noritaka; Synthesis; nb. 17; (2009); p. 2983 - 2991, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.73 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-9.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun-Ichi; Sato, Takaaki; Chida, Noritaka; Synthesis; nb. 17; (2009); p. 2983 - 2991, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

300

Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun-Ichi; Sato, Takaaki; Chida, Noritaka; Synthesis; nb. 17; (2009); p. 2983 - 2991, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun-Ichi; Sato, Takaaki; Chida, Noritaka; Synthesis; nb. 17; (2009); p. 2983 - 2991, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

neat liquid

Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun-Ichi; Sato, Takaaki; Chida, Noritaka; Synthesis; nb. 17; (2009); p. 2983 - 2991, View in Reaxys Mass Spectrometry (1)

208/232

2017-11-12 20:29:58

Description (Mass References Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation); Spectrum

Momose, Takayuki; Kaiya, Yuji; Hasegawa, Jun-Ichi; Sato, Takaaki; Chida, Noritaka; Synthesis; nb. 17; (2009); p. 2983 - 2991, View in Reaxys

Reaxys ID 3637770 View in Reaxys

175/204 CAS Registry Number: 127420-03-5 Chemical Name: (3R,5R,6S)-4-(Benzyloxycarbonyl)-5,6-diphenyl-3-(2'-(5'-methylfuryl))-2,3,5,6-tetrahydro-1,4-oxazin-2one; (3R,5R,6S)-4-(Benzyloxycarbonyl)-5,6-diphenyl-3-[2'-(5'methylfuryl)]-2,3,5,6-tetrahydro-1,4-oxazin-2-one Linear Structure Formula: C29H25NO5 Molecular Formula: C29H25NO5 Molecular Weight: 467.521 Type of Substance: heterocyclic InChI Key: HKFGBTVAPSAJNC-PFBJBMPXSA-N Note:

O O

N O

Substance Label (1) Label References 9

Williams; Hendrix; Journal of Organic Chemistry; vol. 55; nb. 12; (1990); p. 3723 - 3727, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.36

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.98

Lipinski Number

Veber Number

Reaxys ID 6021583 View in Reaxys

176/204 CAS Registry Number: 112741-68-1 Chemical Name: (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-<2'-(5'-methylfuryl)>-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one; (3S,5S,6R)-4-(benzyloxycarbonyl)-5,6-diphenyl-3-[2'(5'-methylfuryl)]-2,3,5,6-tetrahydro-4H-1,4-oxazin-2-one Linear Structure Formula: C29H25NO5 Molecular Formula: C29H25NO5 Molecular Weight: 467.521 Type of Substance: heterocyclic InChI Key: HKFGBTVAPSAJNC-GMQQYTKMSA-N Note:

O O

N O

Substance Label (1) Label References 22

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys

Druglikeness (1) 1 of 1

LogP

5.36

209/232

2017-11-12 20:29:58

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

68.98

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

171 - 172

Solvent (Melting Point)

hexane; ethyl acetate

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.09 g/100ml

Solvent (Optical Rotatory Power)

CH2Cl2

Optical Rotatory Power [deg]

44.7

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

119.9

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Temperature (NMR Spectroscopy) [°C]

119.9

Comment (NMR Spectroscopy)

1H-1H.

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

210/232

2017-11-12 20:29:58

Solvent (IR Spectroscopy)

CH2Cl2

Comment (IR Spectroscopy)

3030 - 1020 cm**(-1)

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys Mass Spectrometry (1) Description (Mass References Spectrometry) spectrum

Williams, Robert M.; Sinclair, Peter J.; Zhai, Dongguan; Chen, Daimo; Journal of the American Chemical Society; vol. 110; nb. 5; (1988); p. 1547 - 1557, View in Reaxys

Reaxys ID 15050827 View in Reaxys

177/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy-(2fluorophenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C25H24FNO7 Molecular Formula: C25H24FNO7 Molecular Weight: 469.466 InChI Key: MGYWTGWMNHXYDG-BVVFMGSASA-N Note:

O O O O OF O

N O

Druglikeness (1) 1 of 1

LogP

4.127

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Reaxys ID 6022381 View in Reaxys

178/204 CAS Registry Number: 103825-76-9 Chemical Name: Z-Pro-OMaq Linear Structure Formula: C28H23NO6 Molecular Formula: C28H23NO6 Molecular Weight: 469.494 Type of Substance: heterocyclic InChI Key: XUWDQMACCIZDBT-DEOSSOPVSA-N Note:

O O

N O

Druglikeness (1) 1 of 1

LogP

4.841

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

89.98

Lipinski Number

211/232

2017-11-12 20:29:58

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

132

Solvent (Melting Point)

ethyl acetate; hexane

Auwera, C. Van der; Anteunis, M. J. O.; Bulletin des Societes Chimiques Belges; vol. 95; nb. 3; (1986); p. 203 206, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

2 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-42.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Auwera, C. Van der; Anteunis, M. J. O.; Bulletin des Societes Chimiques Belges; vol. 95; nb. 3; (1986); p. 203 206, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Auwera, C. Van der; Anteunis, M. J. O.; Bulletin des Societes Chimiques Belges; vol. 95; nb. 3; (1986); p. 203 206, View in Reaxys

Reaxys ID 8941946 View in Reaxys

179/204 CAS Registry Number: 359882-24-9 Chemical Name: (R)-1-benzyloxycarbonyl-2-(2-bromo-4-methoxyphenyl)methyl-2-methoxycarbonyl-4-oxopyrrolidine; (R)-1benzylcarbonyl-2-(2-bromo-4-methoxyphenylmethyl)-2-methoxycarbonyl-4-oxopyrrolidine Linear Structure Formula: C22H22BrNO6 Molecular Formula: C22H22BrNO6 Molecular Weight: 476.324 Type of Substance: heterocyclic InChI Key: VJWDKNQKVXUHRD-JOCHJYFZSA-N Note:

Br O O O O

Substance Label (2) Label References 21

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys

Tamura; Yanagimachi; Kobayashi; Ishibashi; Organic letters; vol. 3; nb. 16; (2001); p. 2427 - 2429, View in Reaxys

Druglikeness (1) 1 of 1

LogP

3.074

H Bond Donors

212/232

2017-11-12 20:29:58

H Bond Acceptors

Rotatable Bonds

TPSA

82.14

Lipinski Number

Veber Number

Optical Rotatory Power (2) 1 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.12 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-85.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys 2 of 2

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.12 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-85.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Tamura; Yanagimachi; Kobayashi; Ishibashi; Organic letters; vol. 3; nb. 16; (2001); p. 2427 - 2429, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

270

Tamura; Yanagimachi; Kobayashi; Ishibashi; Organic letters; vol. 3; nb. 16; (2001); p. 2427 - 2429, View in Reaxys; Tamura, Osamu; Yanagimachi, Takehiko; Ishibashi, Hiroyuki; Tetrahedron Asymmetry; vol. 14; nb. 19; (2003); p. 3033 - 3041, View in Reaxys 2 of 2

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- CDCl3 scopy)

213/232

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Frequency (NMR Spectroscopy) [MHz]

270

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Reaxys ID 13652011 View in Reaxys

180/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy-(2chlorophenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C25H24ClNO7 Molecular Formula: C25H24ClNO7 Molecular Weight: 485.921 InChI Key: MJKVMFMXJZZULO-BVVFMGSASA-N Note:

O O O O O Cl O

N O

Druglikeness (1) 1 of 1

LogP

4.588

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

112 - 115

Patent; Dr. Willmar Schwabe GmbH and Co.; US4965283; (1990); (A1) English, View in Reaxys

Reaxys ID 8592621 View in Reaxys

181/204 Linear Structure Formula: C26H24N2O8 Molecular Formula: C26H24N2O8 Molecular Weight: 492.485 Type of Substance: heterocyclic InChI Key: YUDZYJWFTLAYML-SMXKYELJSA-N Note:

O N

O O

H O

racemate

Druglikeness (1) 1 of 1

LogP

1.715

214/232

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H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

119.52

Lipinski Number

Veber Number

Reaxys ID 15134205 View in Reaxys

182/204 Chemical Name: 1-[(10-chloro-6,7-dihydro-4-oxo-3-phenyl-4Hbenzo[a]quinolizin-1-yl)methyl]2-methyl(R)-1,2-pyrrolidinedicarboxylate Linear Structure Formula: C27H25ClN2O5 Molecular Formula: C27H25ClN2O5 Molecular Weight: 492.959 InChI Key: QBWBGOXICRXQEA-HHHXNRCGSA-N Note:

OH N

N O

Druglikeness (1) 1 of 1

LogP

4.075

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

87.15

Lipinski Number

Veber Number

Reaxys ID 15832873 View in Reaxys

183/204 CAS Registry Number: 1015426-35-3 Linear Structure Formula: C28H24N2O7 Molecular Formula: C28H24N2O7 Molecular Weight: 500.508 InChI Key: WHDPEZUYDPAYEL-QPPBQGQZSA-N Note:

O N O

N O O

O O

Substance Label (1) Label References (4R)-7

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.267

H Bond Donors

H Bond Acceptors

215/232

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Rotatable Bonds

TPSA

102.45

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

124 - 126

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.09 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-44.1

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys

Reaxys ID 15832874 View in Reaxys

184/204 CAS Registry Number: 1015426-48-8 Linear Structure Formula: C28H24N2O7 Molecular Formula: C28H24N2O7 Molecular Weight: 500.508 InChI Key: WHDPEZUYDPAYEL-URXFXBBRSA-N Note:

O N O

N O O

O O

Substance Label (1) Label References (4S)-7

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys

Druglikeness (1)

216/232

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1 of 1

LogP

4.267

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.45

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

130 - 132

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.88 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

-4.2

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys

Reaxys ID 15832875 View in Reaxys

185/204 CAS Registry Number: 1015426-39-7 Linear Structure Formula: C28H24N2O7 Molecular Formula: C28H24N2O7 Molecular Weight: 500.508 InChI Key: WWLSVDPNKNBUDA-ZEQRLZLVSA-N Note:

O O

N O

N O O

O O

Substance Label (1)

217/232

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Label

References

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.267

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.45

Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.65 g/100ml

Solvent (Optical Rotatory Power)

CHCl3

Optical Rotatory Power [deg]

1.25

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- CDCl3 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Liu, Fa; Stephen, Andrew G.; Fisher, Robert J.; Burke Jr., Terrence R.; Bioorganic and Medicinal Chemistry Letters; vol. 18; nb. 3; (2008); p. 1096 - 1101, View in Reaxys

Reaxys ID 5676556 View in Reaxys

186/204

218/232

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CAS Registry Number: 97551-75-2; 97590-62-0 Chemical Name: L-allo-1-(benzyloxycarbonyl)-4-((4-ooazetidin-2-yl)oxy)proline diphenylmethyl ester; L-allo-1-(benzyloxycarbonyl)-4-[(4-ooazetidin-2-yl)oxy]proline diphenylmethyl ester Linear Structure Formula: C29H28N2O6 Molecular Formula: C29H28N2O6 Molecular Weight: 500.551 Type of Substance: heterocyclic InChI Key: QTCZHJQZIIVSBD-OKHNBNEASA-N Note:

N O

O O

Substance Label (1) Label References 22

Bernardo, Silvano De; Tengi, John P.; Sasso, Gino J.; Weigele, Manfred; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3457 - 3462, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.113

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

94.17

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

193 - 195

Bernardo, Silvano De; Tengi, John P.; Sasso, Gino J.; Weigele, Manfred; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3457 - 3462, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Bernardo, Silvano De; Tengi, John P.; Sasso, Gino J.; Weigele, Manfred; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3457 - 3462, View in Reaxys 2 of 2

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Comment (NMR Spectroscopy)

1H-1H

Bernardo, Silvano De; Tengi, John P.; Sasso, Gino J.; Weigele, Manfred; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3457 - 3462, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

CHCl3

Comment (IR Spectroscopy)

3410 - 699 cm**(-1)

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Bernardo, Silvano De; Tengi, John P.; Sasso, Gino J.; Weigele, Manfred; Journal of Organic Chemistry; vol. 50; nb. 19; (1985); p. 3457 - 3462, View in Reaxys

Reaxys ID 10615965 View in Reaxys

O O N

187/204 CAS Registry Number: 883242-24-8 Linear Structure Formula: C23H23N3O10 Molecular Formula: C23H23N3O10 Molecular Weight: 501.45 Type of Substance: heterocyclic InChI Key: VTOGZDGAFBGNCI-IYBDPMFKSA-N Note:

O O

Substance Label (1) Label References 3

Chong, Hyun-Soon; Garmestani, Kayhan; Bryant Jr., L. Henry; Milenic, Diane E.; Overstreet, Terrish; Birch, Noah; Le, Thien; Brady, Erik D.; Brechbiel, Martin W.; Journal of Medicinal Chemistry; vol. 49; nb. 6; (2006); p. 2055 - 2062, View in Reaxys

Druglikeness (1) 1 of 1

LogP

-0.371

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

156.9

Lipinski Number

Veber Number

Melting Point (1) 1 of 1

Melting Point [°C]

196

Solvent (Melting Point)

ethyl acetate; hexane

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Chong, Hyun-Soon; Garmestani, Kayhan; Bryant Jr., L. Henry; Milenic, Diane E.; Overstreet, Terrish; Birch, Noah; Le, Thien; Brady, Erik D.; Brechbiel, Martin W.; Journal of Medicinal Chemistry; vol. 49; nb. 6; (2006); p. 2055 - 2062, View in Reaxys 2 of 3

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

220/232

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3 of 3

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Reaxys ID 6990774 View in Reaxys

188/204 Chemical Name: Pentachlorophenyl ester of benzyloxycarbonyl-L-pyroglutamic acid Linear Structure Formula: C19H12Cl5NO5 Molecular Formula: C19H12Cl5NO5 Molecular Weight: 511.573 Type of Substance: heterocyclic InChI Key: QLKRRKXOTFTVOS-JTQLQIEISA-N Note:

Cl Cl

Cl OO N O O

Druglikeness (1) 1 of 1

LogP

6.063

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

72.91

Lipinski Number

Veber Number

Reaxys ID 15051081 View in Reaxys

189/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy-(2trifluoromethylphenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C26H24F3NO7 Molecular Formula: C26H24F3NO7 Molecular Weight: 519.474 InChI Key: SCCDAPLUQRRZTE-BVVFMGSASA-N Note:

O O O O

F O

N O

Druglikeness (1) 1 of 1

LogP

4.891

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

221/232

2017-11-12 20:29:58

Reaxys ID 15050922 View in Reaxys

190/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy(2,4-dichlorophenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C25H23Cl2NO7 Molecular Formula: C25H23Cl2NO7 Molecular Weight: 520.366 InChI Key: NEOPBMVZQKSASK-BVVFMGSASA-N Note:

O O O O

Cl O Cl O

N O

Druglikeness (1) 1 of 1

LogP

5.21

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Reaxys ID 15050971 View in Reaxys

191/204 Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy(2,5-dichlorophenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C25H23Cl2NO7 Molecular Formula: C25H23Cl2NO7 Molecular Weight: 520.366 InChI Key: FEUKESWRJCGKBY-BVVFMGSASA-N Note:

O O Cl

O O O Cl O

N O

Druglikeness (1) 1 of 1

LogP

5.21

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Reaxys ID 15050832 View in Reaxys

192/204

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Chemical Name: threo-5-[N-benzyloxycarbonyl-L-prolyloxy-(2bromophenyl)-methyl]-4-methoxy-2(5H)-furanone Linear Structure Formula: C25H24BrNO7 Molecular Formula: C25H24BrNO7 Molecular Weight: 530.372 InChI Key: KLQYJBWOMYKPBX-BVVFMGSASA-N Note:

O O O O O Br O

N O

Druglikeness (1) 1 of 1

LogP

4.764

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

91.37

Lipinski Number

Veber Number

Reaxys ID 21751498 View in Reaxys

O O

193/204 CAS Registry Number: 1265173-13-4 Linear Structure Formula: C32H33NO7 Molecular Formula: C32H33NO7 Molecular Weight: 543.617 InChI Key: CZMPTYAYURRQMI-GFLPGQDNSA-N Note:

O N

O OH O

Druglikeness (1) 1 of 1

LogP

5.129

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

102.37

Lipinski Number

Veber Number

Crystal Property Description (1) Colour & Other References Properties colourless

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Length of Path [cm]

223/232

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Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-7.9

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

500

Location

supporting information

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys 2 of 2

Description (NMR Spec- Chemical shifts; Spectrum troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

125

Location

supporting information

Kaiya, Yuji; Hasegawa, Jun-Ichi; Momose, Takayuki; Sato, Takaaki; Chida, Noritaka; Chemistry - An Asian Journal; vol. 6; nb. 1; (2011); p. 209 - 219, View in Reaxys IR Spectroscopy (1) 1 of 1

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

film

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Reaxys ID 20745084 View in Reaxys

194/204

N O O

CAS Registry Number: 1309561-16-7 Linear Structure Formula: C28H22BrNO7 Molecular Formula: C28H22BrNO7 Molecular Weight: 564.389 InChI Key: SCZUAEBWLHPEMI-QFIPXVFZSA-N Note:

Druglikeness (1) 1 of 1

LogP

5.217

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

99.21

Lipinski Number

Veber Number

Mass Spectrometry (1) Description (Mass Location Spectrometry) LCMS (Liquid chromatography mass spectrometry); ESI (Electrospray ionisation)

References

Page/Page column 116

Patent; PRESIDIO PHARMACEUTICALS, INC.; LI, Leping; ZHONG, Min; WO2010/111534; (2010); (A1) English, View in Reaxys

Reaxys ID 29981510 View in Reaxys F

195/204 Linear Structure Formula: C29H25F6NO4 Molecular Formula: C29H25F6NO4 Molecular Weight: 565.512 InChI Key: KBEOZEXFEKDIRS-XHCCPWGMSA-N Note:

F F F

F O

O O

Substance Label (1) Label References compound 95

Patent; OPKO HEALTH INCORPORATED; PALIWAL, SUNIL; REICHARD, GREGORY A; WANG, CHENG; XIAO, DONG; TSUI, HON-CHUNG; SHIH, NENG-YANG; ARREDONDO, JUAN D; WROBLESKI, MICHELLE LACI; PALANI, ANANDAN; (143 pag.); JP5823476; (2015); (B2) Japanese, View in Reaxys

Druglikeness (1) 1 of 1

LogP

6.396

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

55.84

Lipinski Number

Veber Number

Mass Spectrometry (1)

225/232

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Description (Mass Location Spectrometry)

References

electrospray ionisation (ESI); spectrum

Paragraph 0781

Reaxys ID 31835472 View in Reaxys

196/204 Linear Structure Formula: C34H33NO8 Molecular Formula: C34H33NO8 Molecular Weight: 583.638 InChI Key: HRACMWCXAIWGNV-KPURRNSFSA-N Note:

O O

O O O

O O

Substance Label (1) Label References 5b

Patent; Shanghai Zhong Qiang Pharmaceutical Co., Ltd.; Fu Shaojun; Huang Chengjun; Ren Yi; Cai Huirong; Wang Qiong; Yang Xinan; Li Wei; (21 pag.); CN106831737; (2017); (A) Chinese, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.755

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

108.44

Lipinski Number

Veber Number

Reaxys ID 19566727 View in Reaxys

197/204

O O

CAS Registry Number: 1072902-89-6 Chemical Name: N-[(phenylmethoxy)carbonyl]-L-proline(1S)-1-[[(2S,3S)-3-hexyl-4-oxo-2-oxetanyl]methyl]dodecyl ester Linear Structure Formula: C35H55NO6 Molecular Formula: C35H55NO6 Molecular Weight: 585.825 InChI Key: LOOKFQFUBCEXAZ-YDPTYEFTSA-N Note:

Druglikeness (1) 1 of 1

LogP

11.168

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

82.14

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Lipinski Number

Veber Number

Optical Rotatory Power (1) 1 of 1

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

chloroform

Optical Rotatory Power [deg]

-48

Wavelength (Optical Ro- 589 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Ortar, Giorgio; Bisogno, Tiziana; Ligresti, Alessia; Morera, Enrico; Nalli, Marianna; Di Marzo, Vincenzo; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6970 - 6979, View in Reaxys NMR Spectroscopy (2) 1 of 2

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

13C

Solvents (NMR Spectro- chloroform-d1 scopy) Frequency (NMR Spectroscopy) [MHz]

100

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Solvent (IR Spectroscopy)

chloroform

Ortar, Giorgio; Bisogno, Tiziana; Ligresti, Alessia; Morera, Enrico; Nalli, Marianna; Di Marzo, Vincenzo; Journal of Medicinal Chemistry; vol. 51; nb. 21; (2008); p. 6970 - 6979, View in Reaxys

Reaxys ID 21402862 View in Reaxys

198/204

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CAS Registry Number: 1310352-62-5 Linear Structure Formula: C35H55NO6 Molecular Formula: C35H55NO6 Molecular Weight: 585.825 InChI Key: LOOKFQFUBCEXAZ-IHZBLBIESA-N Note:

O N

O O

Druglikeness (1) 1 of 1

LogP

11.168

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

82.14

Lipinski Number

Veber Number

Reaxys ID 9602980 View in Reaxys

199/204 Linear Structure Formula: C32H32N2O11 Molecular Formula: C32H32N2O11 Molecular Weight: 620.613 Type of Substance: heterocyclic InChI Key: PLIHDAJNUUFUOU-OASJLCFRSA-N Note:

O O

OH O

racemate

Substance Label (1) Label References 24

Musicki, Branislav; Periers, Anne-Marie; Piombo, Laurent; Laurin, Patrick; Klich, Michel; Dupuis-Hamelin, Claudine; Lassaigne, Patrice; Bonnefoy, Alain; Tetrahedron Letters; vol. 44; nb. 52; (2003); p. 9259 - 9262, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.049

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

173.92

Lipinski Number

Veber Number

Medchem (1) 1 of 1

Substance Effect

Antibiotic

Bioassay Category

Toxicity/Safety Pharmacology

Bioassay Name

Cell/tumor cell: proliferation/viability/growth

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Bioassay Details

Target : Staphylococcus aureus 011HT3Bioassay : reference: novobiocin (MIC: <= 0.04 μg/mL) in vitro, twofold broth microdilution after 24 h incubation

Substance RN

9602980View in Reaxys

Substance Name

Measurement Parameter

MIC

Unit

mg/L

Quantitative value

Measurement pX

4.19

Reaxys ID 9605043 View in Reaxys

200/204 Linear Structure Formula: C37H40N2O12 Molecular Formula: C37H40N2O12 Molecular Weight: 704.731 Type of Substance: heterocyclic InChI Key: FDTUQABNFFPEQT-DONRQICBSA-N Note:

O O

racemate

Substance Label (1) Label References 23a

Druglikeness (1) 1 of 1

LogP

5.416

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

172.15

Lipinski Number

Veber Number

Reaxys ID 4640957 View in Reaxys

201/204

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CAS Registry Number: 115516-56-8 Linear Structure Formula: C39H43N3O12 Molecular Formula: C39H43N3O12 Molecular Weight: 745.783 Type of Substance: heterocyclic InChI Key: GKZAKOVIMQVFCL-FZICCQAASA-N Note:

O O

O HO

O O

NH N

Substance Label (1) Label References 17

Wakamiya; Yamanoi; Kanou; Shiba; Tetrahedron Letters; vol. 28; nb. 47; (1987); p. 5887 - 5888, View in Reaxys

Druglikeness (1) 1 of 1

LogP

1.997

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

179.47

Lipinski Number

Veber Number

Reaxys ID 6679984 View in Reaxys

202/204 Linear Structure Formula: C40H40N2O14 Molecular Formula: C40H40N2O14 Molecular Weight: 772.763 Type of Substance: heterocyclic InChI Key: BCAVMFYGVZHLPM-SZDUUPLJSA-N Note:

O N

O O O

N O

O O

Substance Label (1) Label References 12

Brown, Allan G.; Moss, Stephen F.; Southgate, Robert; Tetrahedron Letters; vol. 35; nb. 3; (1994); p. 451 - 454, View in Reaxys

Druglikeness (1) 1 of 1

LogP

4.183

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

190.58

Lipinski Number

230/232

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Veber Number

Reaxys ID 9606270 View in Reaxys

203/204 Linear Structure Formula: C44H46N2O12 Molecular Formula: C44H46N2O12 Molecular Weight: 794.855 Type of Substance: heterocyclic InChI Key: RBTIPUSHAGSMQN-DEISDFRDSA-N Note:

O O

racemate

Substance Label (1) Label References 22

Druglikeness (1) 1 of 1

LogP

7.018

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

161.15

Lipinski Number

Veber Number

Reaxys ID 27589076 View in Reaxys

204/204 Linear Structure Formula: C16H21NO3*xClH Molecular Formula: C16H21NO3*(x)ClH InChI Key: KNULFXJMZGINEM-NTISSMGPSA-N Note:

-1 HCl

O O

N O

Substance Label (1) Label References 13

Druglikeness (1) 1 of 1

LogP

2.803

H Bond Donors

H Bond Acceptors

Rotatable Bonds

TPSA

46.61

231/232

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Lipinski Number

Veber Number

Chromatographic Data (1) Chromatographic Original string data LC (Liquid chromatography)

Location

LC-MS tR = 1.602 Paragraph 00113 mm in 2 mm chromatography,

NMR Spectroscopy (1) 1 of 1

Description (NMR Spec- Chemical shifts troscopy) Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- chloroform-d1 scopy) Original Text (NMR Spectroscopy)

‘H NMR (CDC13) 5 7.38-7.30 (m, 5H), 5.16 (s, 2H), 3.78-3.73 (m, 2H), 2.66-2.43 (m, 3H), 1.51 (s, 3H), 0.99 (s, 3H), 0.86 (s, 3H).

Location

Paragraph 00113

Patent; VITAE PHARMACEUTICALS, INC.; CLAREMON, David, A.; DILLARD, Lawrence, Wayne; DONG, Chengguo; FAN, Yi; JIA, Lanqi; LOTESTA, Stephen, D.; MARCUS, Andrew; SINGH, Suresh, B.; TICE, Colin, M.; YUAN, Jing; ZHAO, Wei; ZHENG, Yajun; ZHUANG, Linghang; WO2014/179564; (2014); (A1) English, View in Reaxys Mass Spectrometry (1) Description (Mass Location Spectrometry) liquid chromatog- Paragraph 00113 raphy mass spectrometry (LCMS); electrospray ionisation (ESI); spectrum

232/232

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