16_page_(R)-2-Amino-2-methyl-3-phenylpropanoic acid [C10H13NO2] by Asch

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Date

1 substances in Reaxys

2018-03-20 15h:15m:44s (EST)

NH 2

1. Query

Search as: As drawn AND (IDE.XRN=2803961)

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Reaxys ID 2803961 View in Reaxys

1/1 CAS Registry Number: 17350-84-4 Chemical Name: (R)-2-amino-2-methyl-3-phenylpropanoic acid; (R)-α-methylphenylalaninne; (R)-(+)-2-methyl-3-phenylalanine; (R)-α-methyl-phenylalanine; (R)-α-methylphenylalanine; D-α-methylphenylalanine; α-methylphenylalanine Linear Structure Formula: C6H5CH2C2H3NH2CO2H Molecular Formula: C10H13NO2 Molecular Weight: 179.219 Type of Substance: isocyclic InChI Key: HYOWVAAEQCNGLE-SNVBAGLBSA-N Note:

OH NH 2

Substance Label (15) Label References 8.1.67

Patent; COMENTIS, INC.; ASTELLAS PHARMA INC.; BILCER, Geoffrey, M.; DEVASAMUDRAM, Thippeswamy; LILLY, John, C.; ANKALA, Sudha, V.; MOSKALEV, Nikolai, V.; LIU, Chunfeng; INOUE, Makoto; KAWAKAMI, Shimpei; MUNAKATA, Ryosuke; HAMAJIMA, Toshihiro; WO2012/54510; (2012); (A1) English, View in Reaxys

Carlier, Paul R.; Zhao, Hongwu; MacQuarrie-Hunter, Stephanie L.; DeGuzman, Joseph C.; Hsu, Danny C.; Journal of the American Chemical Society; vol. 128; nb. 47; (2006); p. 15215 - 15220, View in Reaxys

Patent; NAGASE and COMPANY, LTD.; EP1712549; (2006); (A1) English, View in Reaxys

Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943, View in Reaxys

(R)-10

Lee, Mijoon; Kim, Dong H.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 4; (2000); p. 815 - 823, View in Reaxys; Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 2482, View in Reaxys

(R)-9

Wu, Zhong-Liu; Li, Zu-Yi; Chemical Communications; nb. 3; (2003); p. 386 - 387, View in Reaxys

(R)-11

Carlier, Paul R.; Zhao, Hongwu; DeGuzman, Joe; Lam, Polo C.-H.; Journal of the American Chemical Society; vol. 125; nb. 38; (2003); p. 11482 - 11483, View in Reaxys

Wenglowsky, Steve; Journal of the American Chemical Society; vol. 120; nb. 48; (1998); p. 12468 - 12473, View in Reaxys; Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111, View in Reaxys

(R)-1

(R)-7

Casas, Jesus; Najera, Carmen; Sansano, Jose M.; Gonzalez, Jose; Saa, Jose M.; Vega, Manuel; Tetrahedron Asymmetry; vol. 12; nb. 5; (2001); p. 699 - 702, View in Reaxys

(R)-α-Me-Phe

Belokon, Yuri N.; Kochetkov, Konstantin A.; Churkina, Tatiana D.; Ikonnikov, Nikolai S.; Chesnokov, Alexey A.; Larionov, Oleg V.; Singh, Ishwar; Parmar, Virinder S.; Vyskocil, Stepan; Kagan, Henri B.; Journal of Organic Chemistry; vol. 65; nb. 21; (2000); p. 7041 - 7048, View in Reaxys

(R)-7c

Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717, View in Reaxys

Vedejs; Fields; Hayashi; Hitchcock; Powell; Schrimpf; Journal of the American Chemical Society; vol. 121; nb. 11; (1999); p. 2460 - 2470, View in Reaxys

11-free base

Carloni, Armando; Porzi, Gianni; Sandri, Sergio; Tetrahedron Asymmetry; vol. 9; nb. 17; (1998); p. 2987 2998, View in Reaxys

Subramanian, Pullachipatti K.; Woodard, Ronald W.; Journal of Organic Chemistry; vol. 52; nb. 1; (1987); p. 15 - 18, View in Reaxys

Patent-Specific Data (1) References Patent; Nagase Co., Ltd.; RIKEN; Yamamoto, Kenichiro; Kodama, Kazuya; Anzai, Kinsei; Matsuyama, Keisuke; Sasano, Arisue; Hashizume, Yoshinobu; Hume, William Yuwan; Yashio, Keiji; Nozaki, Satoshi; (75 pag.); JP2016/74605; (2016); (A) Japanese, View in Reaxys Druglikeness (1) 1 of 1

LogP

-1.269

H Bond Donors

2/16

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H Bond Acceptors

Rotatable Bonds

TPSA

63.32

Lipinski Number

Veber Number

Derivative (5) Comment (Derivative)

Derivative

References

(R)-α-methyl-phe- Alonso, Francisco; Davies, Stephen G.; Elend, Almut S.; Haggitt, Jane L.; Journal of nylalanine hydro- the Chemical Society - Perkin Transactions 1; nb. 2; (1998); p. 257 - 264, View in Reaxys chloride (R)-α-methyl-phe- Carloni, Armando; Porzi, Gianni; Sandri, Sergio; Tetrahedron Asymmetry; vol. 9; nb. nylalanine hydro- 17; (1998); p. 2987 - 2998, View in Reaxys chloride (R)-α-methyl-phe- Alonso; Davies; Tetrahedron Asymmetry; vol. 6; nb. 2; (1995); p. 353 - 356, nylalanine hydro- View in Reaxys chloride (R)-α-methyl-phe- Belokon', Yuri N.; Chernoglazova, Nina I.; Kochetkov, Constantin A.; Garbalinnylalanine hydro- skaya, Natalia S.; Belikov, Vasili M.; Journal of the Chemical Society, Chemical Comchloride munications; nb. 3; (1985); p. 171 - 172, View in Reaxys Hydrochlorid: <α>(D)20 = +3.4grad (H2O) Purification (1) Purification (method) via reaction with (-)-chlocyphos

Kolb; Barth; Tetrahedron Letters; (1979); p. 2999,3000,3001, View in Reaxys

References Hulst, Ron; Broxterman, Quirinus B.; Kamphuis, Johan; Formaggio, Fernando; Crisma, Marco; Toniolo, Claudio; Kellogg, Richard M.; Tetrahedron Asymmetry; vol. 8; nb. 12; (1997); p. 1987 - 1999, View in Reaxys

Melting Point (6) 1 of 6

Melting Point [°C]

277 - 279

Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; Golfis, Georgia; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4364 - 4373, View in Reaxys 2 of 6

Melting Point [°C]

277 - 279

Solvent (Melting Point)

H2O

Comment (Melting Point)

Decomposition

Melting Point [°C]

288 - 290

Solvent (Melting Point)

propan-2-ol; H2O

Melting Point [°C]

288 - 290

Solvent (Melting Point)

propan-2-ol; H2O

Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923, View in Reaxys 5 of 6

Melting Point [°C]

262 - 263

Comment (Melting Point)

Decomposition

Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447, View in Reaxys

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6 of 6

Melting Point [°C]

279 - 280

Comment (Melting Point)

Decomposition

Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955, View in Reaxys Chromatographic Data (2) Chromatographic Location data HPLC (High performance liquid chromatography)

Paragraph 0133

References Patent; Nagase Co., Ltd.; RIKEN; Yamamoto, Kenichiro; Kodama, Kazuya; Anzai, Kinsei; Matsuyama, Keisuke; Sasano, Arisue; Hashizume, Yoshinobu; Hume, William Yuwan; Yashio, Keiji; Nozaki, Satoshi; (75 pag.); JP2016/74605; (2016); (A) Japanese, View in Reaxys

TLC (Thin layer chromatography)

Remelli, Maurizio; Faccini, Stefania; Conato, Chiara; Chirality; vol. 26; nb. 6; (2014); p. 313 - 318, View in Reaxys

Crystal Property Description (1) Colour & Other Location Properties

References

white

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys

Decomposition (1) 1 of 1

Decomposition [°C]

230 - 233

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys Optical Rotatory Dispersion (1) Comment (Optical References Rotatory Dispersion) 270000 - 700000 nm

Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143, View in Reaxys

Optical Rotatory Power (24) 1 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

water

Optical Rotatory Power [deg]

13.2

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

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 2 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.04 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

21.5

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

Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; Golfis, Georgia; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4364 - 4373, View in Reaxys 3 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.12 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

22.5

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

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.73 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

21.8

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

Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 5 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.25 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

25.6

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

Carlier, Paul R.; Zhao, Hongwu; DeGuzman, Joe; Lam, Polo C.-H.; Journal of the American Chemical Society; vol. 125; nb. 38; (2003); p. 11482 - 11483, View in Reaxys 6 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.00 g/100ml

Length of Path [cm]

5/16

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Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

20.2

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

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.2 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

-17.8

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)

H2O

Optical Rotatory Power [deg]

21.6

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

Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717, View in Reaxys 9 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

Wavelength (Optical Ro- 589 tatory Power) [nm] Vedejs; Fields; Hayashi; Hitchcock; Powell; Schrimpf; Journal of the American Chemical Society; vol. 121; nb. 11; (1999); p. 2460 - 2470, View in Reaxys 10 of 24

Type (Optical Rotatory Power)

[alpha]

6/16

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Concentration (Optical Rotatory Power)

0.2 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

17.8

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

Comment (Optical Rota- ,single stereoisomer tory Power) Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923, View in Reaxys 11 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

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

Alonso, Francisco; Davies, Stephen G.; Elend, Almut S.; Haggitt, Jane L.; Journal of the Chemical Society Perkin Transactions 1; nb. 2; (1998); p. 257 - 264, View in Reaxys 12 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

6.2

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

Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447, View in Reaxys 13 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.51 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

19.01

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

7/16

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Temperature (Optical Rotatory Power) [°C]

Davis, Franklin A.; Liu, Hu; Reddy, G. Venkat; Tetrahedron Letters; vol. 37; nb. 31; (1996); p. 5473 - 5476, View in Reaxys 14 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.11 g/100ml

Length of Path [cm]

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

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

Studer, Armido; Seebach, Dieter; Liebigs Annalen; nb. 2; (1995); p. 217 - 222, View in Reaxys 15 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

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

Alonso; Davies; Tetrahedron Asymmetry; vol. 6; nb. 2; (1995); p. 353 - 356, View in Reaxys 16 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

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

Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys 17 of 24

Type (Optical Rotatory Power)

alpha

Concentration (Optical Rotatory Power)

5 g/l

Length of Path [cm]

Solvent (Optical Rotatory Power)

various solvent(s)

8/16

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Optical Rotatory Power [deg]

4.2

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

Belokon, Yuri N.; Bakhmutov, Vladimir I.; Chernoglazova, Nina I.; Kochetkov, Konstantin A.; Vitt, Sergei V.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988); p. 305 - 312, View in Reaxys 18 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

20.5

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

Ojima, Iwao; Chen, Hauh-Jyun C.; Qiu, Xiaogang; Tetrahedron; vol. 44; nb. 17; (1988); p. 5307 - 5318, View in Reaxys 19 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.01 g/100ml

Solvent (Optical Rotatory Power)

aq. HCl

Optical Rotatory Power [deg]

4.2

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

Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys 20 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

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

Seebach, Dieter; Fadel, Antoine; Helvetica Chimica Acta; vol. 68; (1985); p. 1243 - 1250, View in Reaxys 21 of 24

Type (Optical Rotatory Power)

[alpha]

9/16

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Concentration (Optical Rotatory Power)

0.1 g/100ml

Solvent (Optical Rotatory Power)

methanol

Optical Rotatory Power [deg]

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

Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340, View in Reaxys 22 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.0 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

19.3

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

Anantharamaiah, G. M.; Roeske, Roger W.; Tetrahedron Letters; vol. 23; nb. 33; (1982); p. 3335 - 3336, View in Reaxys 23 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

0.716 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

47.8

Wavelength (Optical Ro- 300 tatory Power) [nm] Temperature (Optical Rotatory Power) [°C]

Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955, View in Reaxys 24 of 24

Type (Optical Rotatory Power)

[alpha]

Concentration (Optical Rotatory Power)

1.066 g/100ml

Solvent (Optical Rotatory Power)

H2O

Optical Rotatory Power [deg]

20.1

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

Kobayashi,M. et al.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 1898 - 1905, View in Reaxys NMR Spectroscopy (28)

10/16

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1 of 28

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

Solvents (NMR Spectro- water-d2 scopy) Frequency (NMR Spectroscopy) [MHz]

400

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 2 of 28

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

13C

Solvents (NMR Spectro- water-d2 scopy) Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 3 of 28

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

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

400

Xu, Peng-Fei; Li, Shuo; Lu, Ta-Jung; Wu, Chen-Chang; Fan, Botao; Golfis, Georgia; Journal of Organic Chemistry; vol. 71; nb. 12; (2006); p. 4364 - 4373, View in Reaxys; Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943, View in Reaxys 4 of 28

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

400

Nucleus (NMR Spectroscopy)

Solvents (NMR Spectro- d(4)-methanol scopy) Frequency (NMR Spectroscopy) [MHz]

400

Original Text (NMR Spectroscopy)

Comment (NMR Spectroscopy)

Signals given

NMR (d4- MeOH, 400 Mhz) δ 7.25-7.17 (m, 3H), 7.12 (d, J= 6.6 Hz, 2H), 3.27 (d, J= 13.4 Hz, 1H), 3.15 (d, J= 13.4 Hz, 1H), 1.45 (s, 9H), 1.39 (s, 3H)

Patent; MERCK and CO., INC.; WO2006/78576; (2006); (A2) English, View in Reaxys

11/16

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6 of 28

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

13C

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

100

Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943, View in Reaxys 7 of 28

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

300

Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 8 of 28

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

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

300

Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys 9 of 28

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

Solvents (NMR Spectro- dimethylsulfoxide-d6 scopy) Carlier, Paul R.; Zhao, Hongwu; DeGuzman, Joe; Lam, Polo C.-H.; Journal of the American Chemical Society; vol. 125; nb. 38; (2003); p. 11482 - 11483, View in Reaxys 10 of 28

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

Carlier, Paul R.; Zhao, Hongwu; DeGuzman, Joe; Lam, Polo C.-H.; Journal of the American Chemical Society; vol. 125; nb. 38; (2003); p. 11482 - 11483, View in Reaxys 12 of 28

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

12/16

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

400

Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111, View in Reaxys 13 of 28

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

400

Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111, View in Reaxys 14 of 28

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

13C

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

67.5

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

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

270

Nucleus (NMR Spectroscopy)

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Frequency (NMR Spectroscopy) [MHz]

270

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

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

200

13/16

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Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

200

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

Coupling Nuclei

Solvents (NMR Spectro- D2O scopy) Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717, View in Reaxys 20 of 28

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

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

200

Comment (NMR Spectroscopy)

single stereoisomer

Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923, View in Reaxys 21 of 28

Nucleus (NMR Spectroscopy)

Coupling Nuclei

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

200

Comment (NMR Spectroscopy)

single stereoisomer

Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923, View in Reaxys 22 of 28

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

Solvents (NMR Spectro- various solvent(s); D2O scopy) Belokon, Yuri N.; Bakhmutov, Vladimir I.; Chernoglazova, Nina I.; Kochetkov, Konstantin A.; Vitt, Sergei V.; et al.; Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999); (1988);

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p. 305 - 312, View in Reaxys; Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447, View in Reaxys 23 of 28

Description (NMR Spec- Spin-spin coupling constants troscopy) Comment (NMR Spectroscopy)

1H-1H. Solvent(s): further solvent(s), D2O

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

Solvents (NMR Spectro- D2O scopy) Ojima, Iwao; Chen, Hauh-Jyun C.; Qiu, Xiaogang; Tetrahedron; vol. 44; nb. 17; (1988); p. 5307 - 5318, View in Reaxys; Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys; Seebach, Dieter; Fadel, Antoine; Helvetica Chimica Acta; vol. 68; (1985); p. 1243 - 1250, View in Reaxys; Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys 25 of 28

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

13C

Solvents (NMR Spectro- D2O scopy) Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys 26 of 28

Description (NMR Spec- Spin-spin coupling constants troscopy) Solvents (NMR Spectro- D2O scopy) Comment (NMR Spectroscopy)

1H-1H

Ojima, Iwao; Chen, Hauh-Jyun C.; Qiu, Xiaogang; Tetrahedron; vol. 44; nb. 17; (1988); p. 5307 - 5318, View in Reaxys; Belokon', Yu. N.; Chernoglazova, N. I.; Bakhmutov, V. I.; Garbalinskaya, N. S.; Belikov, V. M.; Bulletin of the Academy of Sciences of the USSR, Division of Chemical Science (English Translation); vol. 36; nb. 12; (1987); p. 2595 - 2601; Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya; nb. 12; (1987); p. 2798 - 2804, View in Reaxys; Seebach, Dieter; Fadel, Antoine; Helvetica Chimica Acta; vol. 68; (1985); p. 1243 - 1250, View in Reaxys; Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys 27 of 28

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

Solvents (NMR Spectro- D2O scopy) Temperature (NMR Spectroscopy) [°C]

Kabuto, Kuninobu; Sasaki, Yoichi; Tetrahedron Letters; vol. 31; nb. 7; (1990); p. 1031 - 1034, View in Reaxys 28 of 28

Description (NMR Spec- NMR with shift reagents troscopy) Kabuto, Kuninobu; Sasaki, Yoichi; Tetrahedron Letters; vol. 31; nb. 7; (1990); p. 1031 - 1034, View in Reaxys

IR Spectroscopy (3)

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1 of 3

Description (IR Spectroscopy)

Mid IR (MIR); Bands

Solvent (IR Spectroscopy)

potassium bromide

Location

supporting information

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys 2 of 3

Description (IR Spectroscopy)

Bands

Solvent (IR Spectroscopy)

KBr

Shiraiwa, Tadashi; Suzuki, Masahiro; Sakai, Yoshio; Nagasawa, Hisashi; Takatani, Kazuhiro; Noshi, Daisuke; Yamanashi, Kenji; Chemical and pharmaceutical bulletin; vol. 50; nb. 10; (2002); p. 1362 - 1366, View in Reaxys; Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482, View in Reaxys; Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943, View in Reaxys 3 of 3

Description (IR Spectroscopy)

Bands

Comment (IR Spectroscopy)

3550 - 1654 cm**(-1)

Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268, View in Reaxys Mass Spectrometry (3) Description (Mass Location Spectrometry) HRMS (High resolution mass spectrometry); ESI (Electrospray ionisation)

supporting information

LCMS (Liquid chromatography mass spectrometry)

Comment (Mass Spectrometry)

References

mol peak

Green, Jonathan E.; Bender, David M.; Jackson, Stona; O'donnell, Martin J.; Mccarthy, James R.; Organic Letters; vol. 11; nb. 4; (2009); p. 807 - 810, View in Reaxys

Molecular peak

Patent; MERCK and CO., INC.; WO2006/78576; (2006); (A2) English, View in Reaxys

spectrum

Seebach, Dieter; Fadel, Antoine; Helvetica Chimica Acta; vol. 68; (1985); p. 1243 - 1250, View in Reaxys

UV/VIS Spectroscopy (2) 1 of 2

Absorption Maxima (UV/ 252; 258; 264 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

139; 178; 135

Solvent (UV/VIS Spectroscopy)

H2O

Comment (UV/VIS Spectroscopy)

single stereoisomer

Absorption Maxima (UV/ 252; 258; 264 VIS) [nm] Ext./Abs. Coefficient [l·mol-1cm-1]

139; 178; 135

Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923, View in Reaxys

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