(R)-2-Amino-2-methyl-3-phenylpropanoic acid [C10H13NO2] [CAS 17350-84-4; InChIKey HYOWVAAEQC by Asch

Query Query O

Results

Date

105 reactions 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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O N

NH 2

O HO

H 2N

Rx-ID: 44917278 View in Reaxys 1/105 Yield

Conditions & References 2 :N-benzylidenebis-phenylalanine tert-butyl (15.5 mg, 50μmol) (3) in a toluene solution (2.5 ml) (S)-Maruoka catalyst (registered trademark; nagase Co. ; (CAS: 851942-89-7) (18.7 mg, 25μmol) is added, 0 °C cooled by ice bath. An argon atmosphere, adding aq. unsatd. cesium hydroxide (3.75g), 30 minutes at 0 °C is violently agitated. The methyl iodide of 50 mm prepared by adding a toluene solution (40μL, 2μmol), argon atmosphere, a vigorous stirring at 0° C (methyl iodide is added and a reaction start point). In HPLC perfluoroalkylated for confirming the progress of the reaction, the reaction from 5 minutes after the start, after 10 minutes, after 15 minutes, 20 minutes after the sampling is performed and, by calculating a conversion rate of methyl iodide HPLC analysis. The result of monitoring is confirmed by HPLC before the reaction, the reaction mixture from the starting reaction (5 ml) 25 minutes after pouring water, organic layer separates politeness. The optical part (100μL) extracted org. sampled for checking the purity, the remaining organic layer is heated to 60 °C 4N hydrochloric acid (2.5 ml, 10mmol) in addition to, a vigorous stirring at 60° C (after 30 minutes from the start of reaction). With the progress of the hydrolysis reaction for HPLC, in addition to the organic layer is from 5 minutes after 4N hydrochloric acid solution, after 10 minutes, after 15 minutes, 20 minutes after the sampling is performed and, by HPLC analysis, reaction intermediate and tert-butyl biphenylalanine dimethylpolysiloxaness α-α-conversion rate is calculated from a ratio of dalanine dimethylpolysiloxaness-. In addition to the organic layer 25 minutes after 4N hydrochloric acid solution from the agitation is stopped, by separating the water layer, and a purpose compd. (4) (- (S)-α dimethylpolysiloxaness biphenylalanine) obtained as an aqueous solution of a reaction mixture (60 minutes after the start of reaction). In this embodiment, α-methyl iodide biphenylalanine dimethylpolysiloxaness obtained from 94percent yield conversioin.In this embodiment, the optical obtd. compd. for measuring purity, sampled hydroxycitric aq. 1M (0.5 ml) is added to the organic layer, 30 minutes after stirring, tert-butyl ether (0.5 ml) in a washer 3 times. The separated water layer and sodium carbonate (100 mg), ethyl acetate (0.5 ml) is added, 10 min. The organic layer separating, concentrating, hexane/2-propanol concentrated residue is added to the mixed solution of (80/20) (1 ml), and the sample solution, analyzed by HPLC a [Daicel Chiralpak AD-H; eluent: Phenylbicyclohexane/2-propanol = 30/1, velocity 0.5 ml/min; holding time : (R) body = 13.6 min, the body (S) = 20.4 min]. In this embodiment, the purity of the obtained optical 89percent ee. Furthermore, in this embodiment, the conversion rate cycloalkylation obtd. in Table 3, the hydrolysis reaction of the conversion rate is shown in Table 4. Stage 1: With (11bS)-(-)-4,4-dibutyl-4,5-dihydro-2,6-bis(3,4,5-trifluorophenyl)-3H-dinaphth[2,1-c:1′,2′-e]azepinium bromide, cesium hydroxide in toluene, Time= 0.5h, T= 0 °C , Inert atmosphere Stage 2: With hydrogenchloride in water, toluene, Time= 0.5h, T= 60 °C , Inert atmosphere, stereoselective reaction 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

O HO

OH NH 2

O HO

H 2N

Rx-ID: 38033763 View in Reaxys 2/105 Yield

Conditions & References With Merck RP-18 WF254S plates coated with Nτ-n-decyl-L-spinacine and Cu acetate in methanol, water, Resolution of racemate Remelli, Maurizio; Faccini, Stefania; Conato, Chiara; Chirality; vol. 26; nb. 6; (2014); p. 313 - 318 View in Reaxys

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O H

OH NH 2

NH 2

Rx-ID: 30183989 View in Reaxys 3/105 Yield

Conditions & References Stage 1: With (R)-N-(2-benzoylphenyl)-1-(3-fluorobenzyl)pyrrolidine-2-carboxamide, sodium methylate, nickel(II) nitrate in methanol, T= 50 °C Stage 2: With sodium hydroxide in N,N-dimethyl-formamide, Time= 0.166667h, T= 45 - 50 °C , Inert atmosphere, optical yield given as percent ee, enantioselective reaction, Further stages Saghyan, Ashot S.; Dadayan, Ani S.; Dadayan, Slavik A.; Mkrtchyan, Anna F.; Geolchanyan, Arpine V.; Manasyan, Luiza L.; Ajvazyan, Hrant R.; Khrustalev, Victor N.; Hambardzumyan, Hasmik H.; Maleev, Victor I.; Tetrahedron Asymmetry; vol. 21; nb. 24; (2010); p. 2956 - 2965 View in Reaxys

OH NH 2

OH O NH

Rx-ID: 28371524 View in Reaxys 4/105 Yield

Conditions & References

51 %

19.3 :Step 3: After isopropanol was added to an aqueous solution of (2R)-methyl-3-phenyl-[(1'R)-phenylethylamino]propionic acid obtained in Step 2, 20percent palladium-carbon (200 mg, 50percent wet) was added under nitrogen stream. The atmosphere of the reaction vessel was replaced with hydrogen gas, and reaction was carried out at 50°C for 20 hours (conversion ratio: 100percent). After the catalyst was separated by filtration and washed with distilled water, the pH was adjusted to 4.0 by a 30percent aqueous solution of sodium hydroxide. The quantity of αmethyl-phenylalanine in the resulting solution was determined by high performance liquid chromatography as same as in Example 13; and as a result, 154.9 mg of (R) -α-methyl-phenylalanine having an optical purity of 100percent ee was obtained (total yield: 51percent). With hydrogen, palladium on carbon in water, Time= 20h, T= 50 °C Patent; Kaneka Corporation; EP2050738; (2009); (A1) English View in Reaxys

NH 2

O O

H 2N

Rx-ID: 28536157 View in Reaxys 5/105 Yield 81 %

Conditions & References Stage 1: With lithium hydroxide monohydrate in ethanol, water, Time= 48h, T= 25 °C Stage 2: With hydrogenchloride in ethanol, water, pH= 2, optical yield given as percent ee 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

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NH 2

Rx-ID: 10254541 View in Reaxys 6/105 Yield

Conditions & References

86 %

Stage 1: With sodium hydroxide in methanol, acetone, Time= 2h, T= 20 °C Stage 2: With hydrogenchloride, Time= 3h, T= 92 °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

OH NH 2

Rx-ID: 10255147 View in Reaxys 7/105 Yield

Conditions & References

89 %

NH 2

N NH O

Rx-ID: 10471309 View in Reaxys 8/105 Yield

Conditions & References

72 %

With hydrogenchloride, Time= 48h, T= 125 °C 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

OH NH 2

Rx-ID: 12259749 View in Reaxys 9/105 Yield

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2.1: aqueous NaOH / methanol; acetone / 2 h / 20 °C 2.2: 89 percent / aqueous HCl / 3 h / 92 °C With sodium hydroxide, n-butyllithium, diisopropylamine in tetrahydrofuran, methanol, hexane, acetone 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

NH 2

ZnCr-benzoate*3H2O

Rx-ID: 12282294 View in Reaxys 10/105 Yield

Conditions & References Reaction Steps: 2 1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1.5 h / -30 °C 1.2: hexamethylphosphoric triamide / tetrahydrofuran; hexane / -78 °C 1.3: 80 percent / tetrahydrofuran; hexane / 12 h / -78 °C 2.1: aqueous NaOH / methanol; acetone / 2 h / 20 °C 2.2: 86 percent / aqueous HCl / 3 h / 92 °C With sodium hydroxide, n-butyllithium, diisopropylamine in tetrahydrofuran, methanol, hexane, acetone 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 Reaction Steps: 2 1.1: n-BuLi; diisopropylamine / tetrahydrofuran; hexane / 1.5 h / -30 °C 1.2: hexamethylphosphoric triamide / tetrahydrofuran; hexane / -78 °C 1.3: 80 percent / tetrahydrofuran; hexane / 12 h / -78 °C 2.1: aqueous NaOH / methanol; acetone / 2 h / 20 °C 2.2: 86 percent / aqueous HCl / 3 h / 92 °C With sodium hydroxide, n-butyllithium, diisopropylamine in tetrahydrofuran, methanol, hexane, acetone 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

H O

OH NH 2

Rx-ID: 12293168 View in Reaxys 11/105 Yield

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OH NH 2

O O

H 2N

Rx-ID: 24800256 View in Reaxys 12/105 Yield

Conditions & References 34 :To the benzylated product (compound 9) obtained by either one of Example 2, 21 or 22, a 5N potassium hydroxide aqueous solution (an excessive amount with respect to the compound 9) is added, and the mixture is stirred for one hour until the solution becomes uniform on a water bath at 40°C to 50°C. After cooling to room temperature, 2N hydrochloric acid is added until the pH reaches 6.0. After confirming the production of precipitate, the solution is stirred under ice cooling for 30 min. The precipitate is filtered and washed with ethanol (appropriate amount). The crystals are dried at 50°C overnight to give the compound 40 in a good yield and optical purity. Stage 1: With potassium hydroxide, water, Time= 1h, T= 40 - 50 °C Stage 2: With hydrogenchloride, T= 20 °C , pH= 6 Patent; NAGASE and COMPANY, LTD.; EP1712549; (2006); (A1) English View in Reaxys

O NH 2

HN O OH O

Rx-ID: 11045078 View in Reaxys 13/105 Yield

Conditions & References

93 %

With hydrogenchloride, Time= 6h, Heating Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

O Cl

HN O

OH NH 2

Rx-ID: 11578880 View in Reaxys 14/105 Yield

Conditions & References Reaction Steps: 6 1.1: 239 mg / K2CO3 / methanol; H2O / 3 h / 20 °C 2.1: triphenylphosphine; triethylamine; carbon tetrabromide / CH2Cl2 / 0.33 h / 0 °C 3.1: 70 mg / methanol / 12 h / 20 °C 4.1: ozone / CH2Cl2 / 0.17 h / -78 °C 4.2: dimethyl sulfide / CH2Cl2 / 0.17 h / -78 °C 5.1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 6.1: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene, carbon tetrabromide, potassium carbonate, ozone, triethylamine, triphenylphosphine in methanol, dichloromethane, water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

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O O

OH NH 2

N E

Rx-ID: 11578885 View in Reaxys 15/105 Yield

Conditions & References Reaction Steps: 4 1.1: 70 mg / methanol / 12 h / 20 °C 2.1: ozone / CH2Cl2 / 0.17 h / -78 °C 2.2: dimethyl sulfide / CH2Cl2 / 0.17 h / -78 °C 3.1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 4.1: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene, ozone in methanol, dichloromethane, water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

OH NH 2

O E

Rx-ID: 11578889 View in Reaxys 16/105 Yield

Conditions & References Reaction Steps: 3 1.1: ozone / CH2Cl2 / 0.17 h / -78 °C 1.2: dimethyl sulfide / CH2Cl2 / 0.17 h / -78 °C 2.1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 3.1: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene, ozone in dichloromethane, water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

O NH 2

HN O O

Rx-ID: 11578891 View in Reaxys 17/105 Yield

Conditions & References Reaction Steps: 2 1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 2: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene in water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

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OH NH 2

OH E

Rx-ID: 11578899 View in Reaxys 18/105 Yield

Conditions & References Reaction Steps: 7 1.1: CH2Cl2 / 0.17 h / 0 °C 2.1: 239 mg / K2CO3 / methanol; H2O / 3 h / 20 °C 3.1: triphenylphosphine; triethylamine; carbon tetrabromide / CH2Cl2 / 0.33 h / 0 °C 4.1: 70 mg / methanol / 12 h / 20 °C 5.1: ozone / CH2Cl2 / 0.17 h / -78 °C 5.2: dimethyl sulfide / CH2Cl2 / 0.17 h / -78 °C 6.1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 7.1: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene, carbon tetrabromide, potassium carbonate, ozone, triethylamine, triphenylphosphine in methanol, dichloromethane, water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

NH 2 O

NH 2

Rx-ID: 11578907 View in Reaxys 19/105 Yield

Conditions & References Reaction Steps: 5 1.1: triphenylphosphine; triethylamine; carbon tetrabromide / CH2Cl2 / 0.33 h / 0 °C 2.1: 70 mg / methanol / 12 h / 20 °C 3.1: ozone / CH2Cl2 / 0.17 h / -78 °C 3.2: dimethyl sulfide / CH2Cl2 / 0.17 h / -78 °C 4.1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 5.1: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene, carbon tetrabromide, ozone, triethylamine, triphenylphosphine in methanol, dichloromethane, water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

OH NH 2

Rx-ID: 11613086 View in Reaxys 20/105 Yield

Conditions & References Reaction Steps: 8 1.1: (S)-diphenyl(1-methylpyrrolidin-2-yl)methanol / cyclohexane / Heating 1.2: hexane; cyclohexane / 16 h / 5 °C 2.1: CH2Cl2 / 0.17 h / 0 °C

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3.1: 239 mg / K2CO3 / methanol; H2O / 3 h / 20 °C 4.1: triphenylphosphine; triethylamine; carbon tetrabromide / CH2Cl2 / 0.33 h / 0 °C 5.1: 70 mg / methanol / 12 h / 20 °C 6.1: ozone / CH2Cl2 / 0.17 h / -78 °C 6.2: dimethyl sulfide / CH2Cl2 / 0.17 h / -78 °C 7.1: 48 mg / NaClO2; NaH2PO4; 2-methyl-2-butene / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C 8.1: 93 percent / aq. HCl / 6 h / Heating With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, 2-methyl-but-2-ene, carbon tetrabromide, potassium carbonate, (S)-diphenyl(1-methylpyrrolidin-2-yl)methanol, ozone, triethylamine, triphenylphosphine in methanol, dichloromethane, cyclohexane, water, tert-butyl alcohol Ichikawa, Yoshiyasu; Yamauchi, Eiji; Isobe, Minoru; Bioscience, Biotechnology and Biochemistry; vol. 69; nb. 5; (2005); p. 939 - 943 View in Reaxys

OH NH 2

NH HO

Rx-ID: 4108008 View in Reaxys 21/105 Yield

Conditions & References

100 %

With hydrogenchloride, Time= 1.5h, Heating Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111 View in Reaxys

99 %

With hydrogenchloride, Time= 16h, T= 100 °C Studer, Armido; Seebach, Dieter; Liebigs Annalen; nb. 2; (1995); p. 217 - 222 View in Reaxys

82.1 %

With hydrogenchloride, Time= 10h, Heating 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 With hydrogenchloride, Time= 5h, Heating Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447 View in Reaxys

H N

OH NH 2

O N

Rx-ID: 9275153 View in Reaxys 22/105 Yield 95 %

Conditions & References With hydrogenchloride, Time= 3h, Heating Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482 View in Reaxys With hydrogenchloride, Heating Wu, Zhong-Liu; Li, Zu-Yi; Chemical Communications; nb. 3; (2003); p. 386 - 387

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View in Reaxys

OH NH 2

Rx-ID: 9430956 View in Reaxys 23/105 Yield

Conditions & References

50 %

Stage 1: With hydrogenchloride, Time= 72h, Heating Stage 2: With methyloxirane in ethanol, Time= 0.5h, Heating 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

XOOC-CH2-COOX

OH NH 2

Rx-ID: 14082916 View in Reaxys 24/105 Yield

Conditions & References Reaction Steps: 2 1.1: HMPA; LDA / tetrahydrofuran; hexane / 0.25 h 1.2: n-BuLi / tetrahydrofuran; hexane / 0.25 h 1.3: 74 percent / tetrahydrofuran; hexane / 3 h / -78 °C 2.1: aq. HCl / 72 h / Heating 2.2: 50 percent / propylene oxide / ethanol / 0.5 h / Heating With hydrogenchloride, N,N,N,N,N,N-hexamethylphosphoric triamide, lithium diisopropyl amide in tetrahydrofuran, hexane 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

H N

OH NH 2

O N

Rx-ID: 14275734 View in Reaxys 25/105 Yield

Conditions & References Reaction Steps: 2 1: 2 h / 80 °C 2: 95 percent / 20 percent aq. HCl / 3 h / Heating With hydrogenchloride Wu, Zhong-Liu; Li, Zu-Yi; Journal of Organic Chemistry; vol. 68; nb. 6; (2003); p. 2479 - 2482 View in Reaxys

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NH 2

OH NH 2

Rx-ID: 14344465 View in Reaxys 26/105 Yield

Conditions & References Reaction Steps: 5 1.1: aq. NaOH 1.2: petroleum ether / 6 h / Heating 2.1: 22.24 g / CH2Cl2 / 70 h / -50 - 20 °C 3.1: LiN(TMS)2 / tetrahydrofuran / -30 - 20 °C 4.1: 100 percent / KOSiMe3 / tetrahydrofuran / 1 h / 60 °C 5.1: 100 percent / aq. HCl / 1.5 h / Heating With hydrogenchloride, sodium hydroxide, potassium trimethylsilonate, lithium hexamethyldisilazane in tetrahydrofuran, dichloromethane Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111 View in Reaxys

OH NH 2

NH O

Rx-ID: 14360462 View in Reaxys 27/105 Yield

Conditions & References Reaction Steps: 4 1: 22.24 g / CH2Cl2 / 70 h / -50 - 20 °C 2: LiN(TMS)2 / tetrahydrofuran / -30 - 20 °C 3: 100 percent / KOSiMe3 / tetrahydrofuran / 1 h / 60 °C 4: 100 percent / aq. HCl / 1.5 h / Heating With hydrogenchloride, potassium trimethylsilonate, lithium hexamethyldisilazane in tetrahydrofuran, dichloromethane Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111 View in Reaxys

O O

OH NH 2

N O O

Rx-ID: 14364449 View in Reaxys 28/105 Yield

Conditions & References Reaction Steps: 3 1: LiN(TMS)2 / tetrahydrofuran / -30 - 20 °C 2: 100 percent / KOSiMe3 / tetrahydrofuran / 1 h / 60 °C 3: 100 percent / aq. HCl / 1.5 h / Heating With hydrogenchloride, potassium trimethylsilonate, lithium hexamethyldisilazane in tetrahydrofuran

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

OH NH 2

O N O O

Rx-ID: 14364481 View in Reaxys 29/105 Yield

Conditions & References Reaction Steps: 2 1: 100 percent / KOSiMe3 / tetrahydrofuran / 1 h / 60 °C 2: 100 percent / aq. HCl / 1.5 h / Heating With hydrogenchloride, potassium trimethylsilonate in tetrahydrofuran Coe, Diane M; Perciaccante, Rossana; Procopiou, Panayiotis A; Organic and biomolecular chemistry; vol. 1; nb. 7; (2003); p. 1106 - 1111 View in Reaxys O O

O NE

NH 2

H 2N

Rx-ID: 9174601 View in Reaxys 30/105 Yield

Conditions & References Stage 1: With tetrachlorobis(tetrahydrofuran)titanium(IV), (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol, lithium diisopropyl amide in tetrahydrofuran, Time= 0.5h, T= -60 °C Stage 2: in tetrahydrofuran, Time= 12h, T= -15 °C Stage 3: With hydrogenchloride in tetrahydrofuran, water, Time= 10h, Heating Hu, Ai-Guo; Zhang, Ling-Yun; Wang, Shan-Wei; Wang, Ji-Tao; Synthetic Communications; vol. 32; nb. 14; (2002); p. 2143 - 2147 View in Reaxys

{N-({(2S)-2-[1-(4-iPrO-2,3,5,6-tetrafluorobenzyl)pyrrolidine-2carboxamido]phenyl}(phenyl)methylidene)-(S)-alaninatoN,N',N'',O}nickel(II)

OH NH 2

O HO

H 2N

Rx-ID: 9292634 View in Reaxys 31/105 Yield

Conditions & References Stage 1: With sodium hydride in N,N-dimethyl-formamide Stage 2:Acid hydrolysis Belokon; Maleev; Petrosyan; Savel'eva; Ikonnikov; Peregudov; Khrustalev; Saghiyan; Russian Chemical Bulletin; vol. 51; nb. 8; (2002); p. 1593 - 1599 View in Reaxys

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OH NH 2

N O O

Rx-ID: 14517982 View in Reaxys 32/105 Yield

Conditions & References Reaction Steps: 5 1.1: 121 g / pyridine / H2O / 12 h / 20 °C 2.1: aq. NaOH / dioxane / 1 h / 20 °C 2.2: cinchonidine / ethanol / 6 h 2.3: 73.8 percent / aq. HCl / 0.5 h 3.1: 86.2 percent / pyridine / 72 h / 5 °C 4.1: 74.9 percent / NaI; Zn / dimethylformamide / 10 h / 120 °C 5.1: 82.1 percent / HCl / 10 h / Heating With pyridine, hydrogenchloride, sodium hydroxide, sodium iodide, zinc in 1,4-dioxane, water, N,N-dimethyl-formamide 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

O NH 2

H NH O

Rx-ID: 14518326 View in Reaxys 33/105 Yield

Conditions & References Reaction Steps: 6 1.1: Ac2O / 1 h / 95 °C 2.1: 121 g / pyridine / H2O / 12 h / 20 °C 3.1: aq. NaOH / dioxane / 1 h / 20 °C 3.2: cinchonidine / ethanol / 6 h 3.3: 73.8 percent / aq. HCl / 0.5 h 4.1: 86.2 percent / pyridine / 72 h / 5 °C 5.1: 74.9 percent / NaI; Zn / dimethylformamide / 10 h / 120 °C 6.1: 82.1 percent / HCl / 10 h / Heating With pyridine, hydrogenchloride, sodium hydroxide, acetic anhydride, sodium iodide, zinc in 1,4-dioxane, water, N,N-dimethyl-formamide 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

O O

OH NH 2

NH O O

Rx-ID: 14527004 View in Reaxys 34/105 Yield

Conditions & References Reaction Steps: 4 1.1: aq. NaOH / dioxane / 1 h / 20 °C 1.2: cinchonidine / ethanol / 6 h

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1.3: 73.8 percent / aq. HCl / 0.5 h 2.1: 86.2 percent / pyridine / 72 h / 5 °C 3.1: 74.9 percent / NaI; Zn / dimethylformamide / 10 h / 120 °C 4.1: 82.1 percent / HCl / 10 h / Heating With pyridine, hydrogenchloride, sodium hydroxide, sodium iodide, zinc in 1,4-dioxane, N,N-dimethyl-formamide 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 Reaction Steps: 5 1: 92 percent / 2 N NaOH / dioxane / 1 h 3: 76.5 percent / pyridine / 72 h / 0 °C 4: 69.2 percent / NaI, Zn / dimethylformamide / 10 h / 120 °C 5: 4 N HCl / 5 h / Heating With pyridine, hydrogenchloride, sodium hydroxide, sodium iodide, zinc in 1,4-dioxane, N,N-dimethyl-formamide Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447 View in Reaxys

H N O

OH NH 2

Rx-ID: 14528484 View in Reaxys 35/105 Yield

Conditions & References Reaction Steps: 2 1: 74.9 percent / NaI; Zn / dimethylformamide / 10 h / 120 °C 2: 82.1 percent / HCl / 10 h / Heating With hydrogenchloride, sodium iodide, zinc in N,N-dimethyl-formamide 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 Reaction Steps: 2 1: 69.2 percent / NaI, Zn / dimethylformamide / 10 h / 120 °C 2: 4 N HCl / 5 h / Heating With hydrogenchloride, sodium iodide, zinc in N,N-dimethyl-formamide Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447 View in Reaxys

O OH

OH NH 2

NH HO

Rx-ID: 14528502 View in Reaxys 36/105 Yield

Conditions & References Reaction Steps: 3 1: 86.2 percent / pyridine / 72 h / 5 °C 2: 74.9 percent / NaI; Zn / dimethylformamide / 10 h / 120 °C 3: 82.1 percent / HCl / 10 h / Heating With pyridine, hydrogenchloride, sodium iodide, zinc in N,N-dimethyl-formamide

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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 Reaction Steps: 3 1: 76.5 percent / pyridine / 72 h / 0 °C 2: 69.2 percent / NaI, Zn / dimethylformamide / 10 h / 120 °C 3: 4 N HCl / 5 h / Heating With pyridine, hydrogenchloride, sodium iodide, zinc in N,N-dimethyl-formamide Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447 View in Reaxys

OH NH 2

O NH 2

Rx-ID: 14657139 View in Reaxys 37/105 Yield

Conditions & References Reaction Steps: 2 1.1: CH2Cl2 / 5 h / Heating 2.1: lithium diisopropylamide; TiCl4*2THF; (2R,3R)-1,4-dimethoxy-1,1,4,4,-tetraphenylbutane-2,3-diol / tetrahydrofuran / 0.5 h / -60 °C 2.2: tetrahydrofuran / 12 h / -15 °C 2.3: hydrochloric acid / tetrahydrofuran; H2O / 10 h / Heating With tetrachlorobis(tetrahydrofuran)titanium(IV), (2R,3R)-1,4-dimethoxy-1,1,4,4-tetraphenyl-2,3-butandiol, lithium diisopropyl amide in tetrahydrofuran, dichloromethane Hu, Ai-Guo; Zhang, Ling-Yun; Wang, Shan-Wei; Wang, Ji-Tao; Synthetic Communications; vol. 32; nb. 14; (2002); p. 2143 - 2147 View in Reaxys

OH NH 2

O HO

H 2N

Rx-ID: 8520466 View in Reaxys 38/105 Yield 40 %

Conditions & References Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Alkylation, benzylation Stage 2: With hydrogenchloride in water, toluene, Heating, Hydrolysis Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923 View in Reaxys Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Alkylation, benzylation Stage 2: With hydrogenchloride in water, toluene, Heating, Hydrolysis, Title compound not separated from byproducts Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923 View in Reaxys Stage 1: With sodium hydroxide, (S)-3,3'-bis[(diethylamino)methyl]-2,2'-dihydroxy-1,1'-binaphthalene in toluene, Time= 40h, T= 20 °C Stage 2: With hydrogenchloride in water, Time= 1h, Heating Stage 3: With methyloxirane in ethanol, Time= 0.5h, Heating, Title compound not separated from byproducts

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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

O Cl O

NH 2

O HO

H 2N

Rx-ID: 8786317 View in Reaxys 39/105 Yield

Conditions & References With hydrogenchloride, Heating Belokon, Yuri N; North, Michael; Churkina, Tatiana D; Ikonnikov, Nikolai S; Maleev, Victor I; Tetrahedron; vol. 57; nb. 13; (2001); p. 2491 - 2498 View in Reaxys

O NH 2

NH O

Rx-ID: 4200632 View in Reaxys 40/105 Yield

Conditions & References

90 %

Stage 1: With hydrogenchloride in 1,4-dioxane, Time= 20h, T= 100 °C , Substitution Stage 2: With methyloxirane in ethanol, Time= 0.5h, Heating, Substitution Lee, Mijoon; Kim, Dong H.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 4; (2000); p. 815 - 823 View in Reaxys With hydrogenchloride in 1,4-dioxane, Time= 12h, T= 100 °C Obrecht; Bohdal; Broger; Bur; Lehmann; Ruffieux; Schonholzer; Spiegler; Muller; Helvetica Chimica Acta; vol. 78; nb. 3; (1995); p. 563 - 580 View in Reaxys

O HO

H N

N H

OH NH 2

N H

Rx-ID: 8592923 View in Reaxys 41/105 Yield

Conditions & References With carboxypeptidase A in water, T= 25 °C , pH= 7.5, Hydrolysis, Enzyme kinetics Lee, Mijoon; Kim, Dong H.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 4; (2000); p. 815 - 823 View in Reaxys

O O

NH 2

N O

O HO

H 2N

Rx-ID: 8688344 View in Reaxys 42/105

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Yield

Conditions & References Stage 1: With sodium hydride, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Substitution Stage 2: With hydrogenchloride in water, Time= 0.25h, Hydrolysis, Further stages. Title compound not separated from byproducts. 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

OH NH 2

N O

O HO

H 2N

Rx-ID: 8688448 View in Reaxys 43/105 Yield 40 %

Conditions & References Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Substitution Stage 2: With hydrogenchloride in water, Time= 0.25h, Hydrolysis 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 Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Substitution Stage 2: With hydrogenchloride in water, Time= 0.25h, Hydrolysis, Title compound not separated from byproducts 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

O O

NH 2

N O

O HO

H 2N

Rx-ID: 8688461 View in Reaxys 44/105 Yield

Conditions & References Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Substitution Stage 2: With hydrogenchloride in water, Time= 0.25h, Hydrolysis, Further stages. Title compound not separated from byproducts. 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

O Br

NH 2

N O

O HO

H 2N

Rx-ID: 8688462 View in Reaxys 45/105

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Yield

Conditions & References Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Substitution Stage 2: With hydrogenchloride in water, Time= 0.25h, Hydrolysis, Further stages. Title compound not separated from byproducts. 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

O H N

OH NH 2

Rx-ID: 15885128 View in Reaxys 46/105 Yield

Conditions & References Reaction Steps: 2 1.1: 70 percent / CF3SO3H / 20 h / 80 °C 2.1: HCl / dioxane / 20 h / 100 °C 2.2: 90 percent / propylene oxide / ethanol / 0.5 h / Heating With hydrogenchloride, trifluorormethanesulfonic acid in 1,4-dioxane, 1.1: Substitution / 2.1: Substitution / 2.2: Substitution Lee, Mijoon; Kim, Dong H.; Bioorganic and Medicinal Chemistry; vol. 8; nb. 4; (2000); p. 815 - 823 View in Reaxys

NH 2

Rx-ID: 5119969 View in Reaxys 47/105 Yield

Conditions & References

76 %

With hydrogenchloride, water, Time= 24h, T= 150 °C Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717 View in Reaxys

E N+ B– O

OH NH 2

Rx-ID: 5171881 View in Reaxys 48/105 Yield

Conditions & References With methanol, ethylenediamine, 1.) reflux, 2 h, 2.) reflux, 1.5 h, Yield given, Multistep reaction Vedejs; Fields; Hayashi; Hitchcock; Powell; Schrimpf; Journal of the American Chemical Society; vol. 121; nb. 11; (1999); p. 2460 - 2470

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View in Reaxys

OH NH 2

Rx-ID: 8520465 View in Reaxys 49/105 Yield 61 %

O O

NH 2

O HO

H 2N

Rx-ID: 8520467 View in Reaxys 50/105 Yield

Conditions & References Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Alkylation, benzylation Stage 2: With hydrogenchloride in water, toluene, Heating, Hydrolysis, Title compound not separated from byproducts Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923 View in Reaxys

O Br

OH NH 2

O HO

H 2N

Rx-ID: 8520468 View in Reaxys 51/105 Yield

Conditions & References Stage 1: With sodium hydroxide, (R,R)-TADDOL in toluene, Time= 12h, T= 15 - 20 °C , Alkylation, benzylation Stage 2: With hydrogenchloride in water, toluene, Heating, Hydrolysis, Title compound not separated from byproducts Belokon'; Kochetkov; Churkina; Ikonnikov; Chesnokov; Larionov; Kagan; Russian Chemical Bulletin; vol. 48; nb. 5; (1999); p. 917 - 923 View in Reaxys

t-BuOCOCH2-X

OH NH 2

Rx-ID: 16220046 View in Reaxys 52/105

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Yield

Conditions & References Reaction Steps: 2 1: 1.) LHMDS / 1.) THF, -40 deg C, 2.) THF, from -40 deg C to 0 deg C, 5 h 2: 57 percent aq. HI / 12 h / Heating With hydrogen iodide, lithium hexamethyldisilazane Carloni, Armando; Porzi, Gianni; Sandri, Sergio; Tetrahedron Asymmetry; vol. 9; nb. 17; (1998); p. 2987 - 2998 View in Reaxys Reaction Steps: 2 1: 75 percent / TBAB, K2CO3 / acetonitrile / 8 h / Ambient temperature 2: 76 percent / HCl, H2O / 24 h / 150 °C With hydrogenchloride, tetrabutylammomium bromide, water, potassium carbonate in acetonitrile Chinchilla, Rafael; Galindo, Nuria; Najera, Carmen; Synthesis; nb. 4; (1999); p. 704 - 717 View in Reaxys

H HO

NH 2 NH 2

Rx-ID: 4878299 View in Reaxys 53/105 Yield

Conditions & References Yield given. Multistep reaction 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

OH NH 2

N O

OH O

Rx-ID: 5123354 View in Reaxys 54/105 Yield

Conditions & References With hydrogen, palladium dihydroxide Wenglowsky, Steve; Journal of the American Chemical Society; vol. 120; nb. 48; (1998); p. 12468 - 12473 View in Reaxys

O N

OH NH 2

Rx-ID: 5235804 View in Reaxys 55/105 Yield

Conditions & References With hydrogen iodide, Time= 12h, Heating Carloni, Armando; Porzi, Gianni; Sandri, Sergio; Tetrahedron Asymmetry; vol. 9; nb. 17; (1998); p. 2987 - 2998 View in Reaxys

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OH NH 2

Na +

NH O–

Rx-ID: 5240459 View in Reaxys 56/105 Yield

Conditions & References

90 %

With hydrogen, palladium dihydroxide in ethanol, Time= 12h, p= 2585.74Torr Carloni, Armando; Porzi, Gianni; Sandri, Sergio; Tetrahedron Asymmetry; vol. 9; nb. 17; (1998); p. 2987 - 2998 View in Reaxys

OH NH 2

Rx-ID: 7789534 View in Reaxys 57/105 Yield

Conditions & References Kolb; Barth; Tetrahedron Letters; (1979); p. 2999,3000,3001 View in Reaxys 11 : (R)-(+)-α-Methylphenylalanine EXAMPLE 11 (R)-(+)-α-Methylphenylalanine Starting with 3.0 g of (2S,4R)-4-benzyl-2-ferrocenyl-4-methyl-3-pivaloyl-1,3-oxazolidin-5-one from Example 3 and following the above general hydrolysis procedure, ferrocenecarboxaldehyde (0.89 g, 76percent) and free amino acid were obtained. The latter was dissolved in methanol and passed through a sinter containing decolourising charcoal to yield, after removing the solvent, the title compound (0.89 g, 76percent) as colourless crystals; [α]578 25 +17 (c 0.1, MeOH) F. W. Bollinger J. Med. Chem. 1971, 14, 373 and D. Seebach, A. Fadel Helv. Chim. Acta 1985, 68, 1243 give m.p. 307°-308° C. dec. and [α]578 24 +20 (c 0.1[MeOH)]. This product proved difficult to dehydrate, showed a tendency to rehydrate, and was easily oxidisable by air. The corresponding hydrochloride was prepared as described by Bollinger (op. cit.); νmax (KBr disc) 3436 (N--H), 3034 (HC=C), 1619 (CO2 -) and 1583 (C=C) cm-1; δH (200 MHz; CH3 OD) 1.50 (3H, S, CH3), 2.92 (1H, d, J 14 Hz, CHA HB), 3.28 (1H, d, J 14 Hz, CHA HB) and 7.29 (5H, m, C6 H5); δc (50.3 MHz, CH3 OD) 21.5 (CH3), 42.6 (CH2), 60.7 (CCH3), 127.6, 128.7, 130.2, 134.1 (5*CCH in C6 H5) and 173.9 (C=O); m/z 180 (M+H)+,[100percent], 134[16] and 88[21]; (Found: C, 55.86; H, 6.77; N, 6.72; C10 H14 NO2 Cl requires C, 55.69; H, 6.54; N, 6.49percent) Patent; Oxford Asymmetry International PLC.; US5801248; (1998); (A1) English View in Reaxys 6 : (R)-(α-Methyl)phenylalanine 200 milligrams of the foregoing (R)-N-carbobenzyloxy-(α-methyl)phenylalanine is mixed together with 20 milligrams of 10 percent palladium on carbon catalyst and 10 milliliters of methanol and subjected to hydrogen pressure of 40 psi for 3 hours. The catalyst is then removed by filtration and the filtrate concentrated in vacuo to obtain a (R)-(α-methyl)phenylalanine product. The product obtained by alkylation of (S)-alanine with benzyl bromide is an optical isomer of the product obtained in Example 2 by the alkylation of (S)-phenylalanine with methyl chloride. Patent; Merck and Co., Inc.; US4508921; (1985); (A1) English View in Reaxys

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OH NH 2

N O

O O

Rx-ID: 16454889 View in Reaxys 58/105 Yield

Conditions & References Reaction Steps: 2 1: NaClO2, NaH2PO4 2: H2 / Pd(OH)2 With sodium chlorite, sodium dihydrogenphosphate, hydrogen, palladium dihydroxide Wenglowsky, Steve; Journal of the American Chemical Society; vol. 120; nb. 48; (1998); p. 12468 - 12473 View in Reaxys

OH NH 2

N E

Rx-ID: 16459177 View in Reaxys 59/105 Yield

Conditions & References Reaction Steps: 3 1: 1 N aq. HCl / tetrahydrofuran 2: NaClO2, NaH2PO4 3: H2 / Pd(OH)2 With hydrogenchloride, sodium chlorite, sodium dihydrogenphosphate, hydrogen, palladium dihydroxide in tetrahydrofuran Wenglowsky, Steve; Journal of the American Chemical Society; vol. 120; nb. 48; (1998); p. 12468 - 12473 View in Reaxys

O HO

OH NH 2

H 2N

Rx-ID: 4726566 View in Reaxys 60/105 Yield

Conditions & 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

O O

NH 2

NH O

Rx-ID: 4701673 View in Reaxys 61/105

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Yield

Conditions & References

74 %

With hydrogen bromide, phenol, Heating Davis, Franklin A.; Liu, Hu; Reddy, G. Venkat; Tetrahedron Letters; vol. 37; nb. 31; (1996); p. 5473 - 5476 View in Reaxys

O E

NH 2

Rx-ID: 17343877 View in Reaxys 62/105 Yield

Conditions & References Reaction Steps: 4 1: 1.) lithium bis(trimethylsilylamide) / 1.) THF, -78 deg C, 30 min; 2.) THF, -78 deg C, 1 h 2: 99 percent / m-CPBA 3: 99 percent / H2 / Pd(black) / formic acid; ethanol / r.t., 8 h then 75 deg C, 1.5 h 4: 74 percent / 48 percent HBr, phenol / Heating With hydrogen bromide, hydrogen, 3-chloro-benzenecarboperoxoic acid, lithium hexamethyldisilazane, phenol, palladium in formic acid, ethanol Davis, Franklin A.; Liu, Hu; Reddy, G. Venkat; Tetrahedron Letters; vol. 37; nb. 31; (1996); p. 5473 - 5476 View in Reaxys

OH NH 2

N S O

O O

Rx-ID: 17366159 View in Reaxys 63/105 Yield

Conditions & References Reaction Steps: 3 1: 99 percent / m-CPBA 2: 99 percent / H2 / Pd(black) / formic acid; ethanol / r.t., 8 h then 75 deg C, 1.5 h 3: 74 percent / 48 percent HBr, phenol / Heating With hydrogen bromide, hydrogen, 3-chloro-benzenecarboperoxoic acid, phenol, palladium in formic acid, ethanol Davis, Franklin A.; Liu, Hu; Reddy, G. Venkat; Tetrahedron Letters; vol. 37; nb. 31; (1996); p. 5473 - 5476 View in Reaxys

OH NH 2

O O

Rx-ID: 17366335 View in Reaxys 64/105 Yield

Conditions & References Reaction Steps: 2 1: 99 percent / H2 / Pd(black) / formic acid; ethanol / r.t., 8 h then 75 deg C, 1.5 h 2: 74 percent / 48 percent HBr, phenol / Heating With hydrogen bromide, hydrogen, phenol, palladium in formic acid, ethanol Davis, Franklin A.; Liu, Hu; Reddy, G. Venkat; Tetrahedron Letters; vol. 37; nb. 31; (1996); p. 5473 - 5476 View in Reaxys

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O OH

NH 2

NH HO

Rx-ID: 17592902 View in Reaxys 65/105 Yield

Conditions & References Reaction Steps: 4 2: 76.5 percent / pyridine / 72 h / 0 °C 3: 69.2 percent / NaI, Zn / dimethylformamide / 10 h / 120 °C 4: 4 N HCl / 5 h / Heating With pyridine, hydrogenchloride, sodium iodide, zinc in N,N-dimethyl-formamide Olma; Polish Journal of Chemistry; vol. 70; nb. 11; (1996); p. 1442 - 1447 View in Reaxys

O O O

OH NH 2

N H

H 2N

Rx-ID: 4109122 View in Reaxys 66/105 Yield

Conditions & References With hydrogenchloride, Time= 7h, T= 120 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Berkowitz, David B.; Smith, Marianne K.; Journal of Organic Chemistry; vol. 60; nb. 5; (1995); p. 1233 - 1238 View in Reaxys

(2S,4R)-4-benzyl-2-ferrocenyl-4-methyl-3pivaloyl-1,3-oxazolidin-5-one

OH NH 2

Rx-ID: 7789535 View in Reaxys 67/105 Yield

Conditions & References With amberlyst-15, water in acetone, Yield given Alonso; Davies; Tetrahedron Asymmetry; vol. 6; nb. 2; (1995); p. 353 - 356 View in Reaxys

OH NH 2

NH H 2N

Rx-ID: 18116891 View in Reaxys 68/105 Yield

Conditions & References Reaction Steps: 3 1: 94 percent / NEt3, 4-(dimethylamino)pyridine / CH2Cl2 / 0 deg C to room temp.; 12 h at room temp. 2: 96 percent / 4 N HCl / dioxane / 4 h / 80 °C 3: 99 percent / conc. aq. HCl / 16 h / 100 °C

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With hydrogenchloride, dmap, triethylamine in 1,4-dioxane, dichloromethane Studer, Armido; Seebach, Dieter; Liebigs Annalen; nb. 2; (1995); p. 217 - 222 View in Reaxys

O NH 2

NH O

Rx-ID: 18121157 View in Reaxys 69/105 Yield

Conditions & References Reaction Steps: 2 1: 96 percent / 4 N HCl / dioxane / 4 h / 80 °C 2: 99 percent / conc. aq. HCl / 16 h / 100 °C With hydrogenchloride in 1,4-dioxane Studer, Armido; Seebach, Dieter; Liebigs Annalen; nb. 2; (1995); p. 217 - 222 View in Reaxys

O O

OH NH 2

O N

N O

Rx-ID: 18124621 View in Reaxys 70/105 Yield

Conditions & References Reaction Steps: 4 1: 79 percent / 6N HCl / methanol / Heating 2: 94 percent / NEt3, 4-(dimethylamino)pyridine / CH2Cl2 / 0 deg C to room temp.; 12 h at room temp. 3: 96 percent / 4 N HCl / dioxane / 4 h / 80 °C 4: 99 percent / conc. aq. HCl / 16 h / 100 °C With hydrogenchloride, dmap, triethylamine in 1,4-dioxane, methanol, dichloromethane Studer, Armido; Seebach, Dieter; Liebigs Annalen; nb. 2; (1995); p. 217 - 222 View in Reaxys

O O

OH NH 2

HN O

Rx-ID: 3678668 View in Reaxys 71/105 Yield 94 %

Conditions & References With hydrogenchloride, Time= 2h, Heating Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268 View in Reaxys

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O NH 2

HO N

Rx-ID: 18432939 View in Reaxys 72/105 Yield

Conditions & References Reaction Steps: 4 1: aq. NaOH, 30percent aq. H2O2 / 12 h 2: diethyl ether 3: 98 percent / Hg(OAc)2, NBS / dimethylformamide / 12 h / Ambient temperature 4: 94 percent / 20percent aq. HCl / 2 h / Heating With hydrogenchloride, sodium hydroxide, N-Bromosuccinimide, mercury(II) diacetate, dihydrogen peroxide in diethyl ether, N,N-dimethyl-formamide Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268 View in Reaxys

H O

O O

OH NH 2

O N

Rx-ID: 18440889 View in Reaxys 73/105 Yield

Conditions & References Reaction Steps: 5 1: 93 percent / KOH / methanol / 5 h / Heating 2: aq. NaOH, 30percent aq. H2O2 / 12 h 3: diethyl ether 4: 98 percent / Hg(OAc)2, NBS / dimethylformamide / 12 h / Ambient temperature 5: 94 percent / 20percent aq. HCl / 2 h / Heating With hydrogenchloride, potassium hydroxide, sodium hydroxide, N-Bromosuccinimide, mercury(II) diacetate, dihydrogen peroxide in methanol, diethyl ether, N,N-dimethyl-formamide Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268 View in Reaxys

O O H 2N

OH NH 2

Rx-ID: 18443644 View in Reaxys 74/105 Yield

Conditions & References Reaction Steps: 2 1: 98 percent / Hg(OAc)2, NBS / dimethylformamide / 12 h / Ambient temperature 2: 94 percent / 20percent aq. HCl / 2 h / Heating With hydrogenchloride, N-Bromosuccinimide, mercury(II) diacetate in N,N-dimethyl-formamide Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268 View in Reaxys

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NH 2

H 2N O OH

Rx-ID: 18447409 View in Reaxys 75/105 Yield

Conditions & References Reaction Steps: 3 1: diethyl ether 2: 98 percent / Hg(OAc)2, NBS / dimethylformamide / 12 h / Ambient temperature 3: 94 percent / 20percent aq. HCl / 2 h / Heating With hydrogenchloride, N-Bromosuccinimide, mercury(II) diacetate in diethyl ether, N,N-dimethyl-formamide Cativiela; Diaz-de-Villegas; Galvez; Tetrahedron Asymmetry; vol. 5; nb. 2; (1994); p. 261 - 268 View in Reaxys

O O O

OH NH 2

H 2N

Rx-ID: 2459937 View in Reaxys 76/105 Yield

Conditions & References With lithium hydroxide in 1,4-dioxane, water, Time= 0.333333h, T= 25 °C , Yield given. Yields of byproduct given. Title compound not separated from byproducts Zydowsky; De Lara; Spanton; Journal of Organic Chemistry; vol. 55; nb. 20; (1990); p. 5437 - 5439 View in Reaxys

O O

NH 2

O O

Rx-ID: 21775850 View in Reaxys 77/105 Yield

Conditions & References Reaction Steps: 2 1: 1) LiHMDS, 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone / 1) THF, -78 deg C, 15 min 2) -78 to -30 deg C, 2h 2: LiOH / dioxane; H2O / 0.33 h / 25 °C With 1,3 -dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone, lithium hydroxide, lithium hexamethyldisilazane in 1,4-dioxane, water Zydowsky; De Lara; Spanton; Journal of Organic Chemistry; vol. 55; nb. 20; (1990); p. 5437 - 5439 View in Reaxys

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OH NH 2

O HO

OH N H

HN HO

H 2N

Rx-ID: 3196645 View in Reaxys 78/105 Yield

Conditions & References

43 %

With potassium hydroxide, porcine kidney acylase I, pH 7.5-8.0 Chenault, H. Keith; Dahmer, Juergen; Whitesides, George M.; Journal of the American Chemical Society; vol. 111; nb. 16; (1989); p. 6354 - 6364 View in Reaxys With potassium hydroxide, porcine kidney acylase I, pH 7.5-8.0, Yield given. Yields of byproduct given Chenault, H. Keith; Dahmer, Juergen; Whitesides, George M.; Journal of the American Chemical Society; vol. 111; nb. 16; (1989); p. 6354 - 6364 View in Reaxys

H 2N

OH NH 2

H 2N

Rx-ID: 2394235 View in Reaxys 79/105 Yield

Conditions & References Yield given. Multistep reaction. Yields of byproduct given 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 Yield given. Multistep reaction Belokon', Yuri N.; Chernoglazova, Nina I.; Kochetkov, Constantin A.; Garbalinskaya, Natalia S.; Belikov, Vasili M.; Journal of the Chemical Society, Chemical Communications; nb. 3; (1985); p. 171 - 172 View in Reaxys

O NH 2

O HN

O HO

H 2N

Rx-ID: 2660087 View in Reaxys 80/105 Yield

Conditions & References With hydrogen cation, methyloxirane, 2.) ethanol, Yield given. Multistep reaction. Yields of byproduct given. Title compound not separated from byproducts Georg, Gunda I.; Guan, Xiangming; Kant, Joydeep; Tetrahedron Letters; vol. 29; nb. 4; (1988); p. 403 - 406 View in Reaxys

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OH O

NH 2

O O

N H

O O

Rx-ID: 3001632 View in Reaxys 81/105 Yield

Conditions & References

85.5 %

With hydrogenchloride in tetrahydrofuran, water, Time= 48h, T= 120 °C Ojima, Iwao; Chen, Hauh-Jyun C.; Qiu, Xiaogang; Tetrahedron; vol. 44; nb. 17; (1988); p. 5307 - 5318 View in Reaxys With hydrogenchloride in tetrahydrofuran, water, T= 110 °C Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys

NH 2

H 2N O

H 2N

Rx-ID: 3037102 View in Reaxys 82/105 Yield

Conditions & References With hydrogenchloride, Time= 72h, T= 90 °C Kruizinga, Wim H.; Bolster, John; Kellogg, Richard M.; Kamphuis, Johan; Boesten, Wilhelmus H. J.; et al.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1826 - 1827 View in Reaxys

O NH 2

N O O

Rx-ID: 19501868 View in Reaxys 83/105 Yield

Conditions & References Reaction Steps: 2 1: H2 / Pd-C 2: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C With hydrogenchloride, hydrogen, palladium on activated charcoal in tetrahydrofuran, water Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys Reaction Steps: 3 1: CF3COOH 2: Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 3: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C With hydrogenchloride, ammonia, lithium, trifluoroacetic acid in tetrahydrofuran, water, tert-butyl alcohol Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys

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Reaction Steps: 2 1: 99 percent / H2 / 10percent Pd/C / methanol / 8 h / 50 °C 2: 85.5 percent / 6N HCl / tetrahydrofuran; H2O / 48 h / 120 °C With hydrogenchloride, hydrogen, palladium on activated charcoal in tetrahydrofuran, methanol, water Ojima, Iwao; Chen, Hauh-Jyun C.; Qiu, Xiaogang; Tetrahedron; vol. 44; nb. 17; (1988); p. 5307 - 5318 View in Reaxys

H 2N O

OH NH 2

H 2N

Rx-ID: 20474257 View in Reaxys 84/105 Yield

Conditions & References Reaction Steps: 2 1: H2O / 72 h / 37 °C / aminopeptidase from Mycobacterium neoaurum ATCC 25795 2: 6 N HCl / 72 h / 90 °C With hydrogenchloride, water Kruizinga, Wim H.; Bolster, John; Kellogg, Richard M.; Kamphuis, Johan; Boesten, Wilhelmus H. J.; et al.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1826 - 1827 View in Reaxys Reaction Steps: 2 2: 6 N HCl / 72 h / 90 °C With hydrogenchloride Kruizinga, Wim H.; Bolster, John; Kellogg, Richard M.; Kamphuis, Johan; Boesten, Wilhelmus H. J.; et al.; Journal of Organic Chemistry; vol. 53; nb. 8; (1988); p. 1826 - 1827 View in Reaxys

OH NH 2

Rx-ID: 20793324 View in Reaxys 85/105 Yield

Conditions & References Reaction Steps: 3 1: 1.) LDA / 1.) THF, n-hexane, 0-5 degC, 5 min.; 2.) -78 degC, 5 h 2: 99 percent / H2 / 10percent Pd/C / methanol / 8 h / 50 °C 3: 85.5 percent / 6N HCl / tetrahydrofuran; H2O / 48 h / 120 °C With hydrogenchloride, hydrogen, lithium diisopropyl amide, palladium on activated charcoal in tetrahydrofuran, methanol, water Ojima, Iwao; Chen, Hauh-Jyun C.; Qiu, Xiaogang; Tetrahedron; vol. 44; nb. 17; (1988); p. 5307 - 5318 View in Reaxys Reaction Steps: 3 1: 1) K-hexamethyldisilazide / 1) THF-toluene, -78 deg C, 5 min 2) warming up to rt. 2: 1N NaOH / methanol / Ambient temperature 3: H2 / 10percent Pd/C / methanol / 2 h / 206.9 Torr With sodium hydroxide, K-hexamethyldisilazide, hydrogen, palladium on activated charcoal in methanol Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340 View in Reaxys

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OH NH 2

O O O

Rx-ID: 21489979 View in Reaxys 86/105 Yield

Conditions & References Reaction Steps: 2 1: 95 percent / methanesulfonic acid, sodium azide / CHCl3 / 1 h / Heating 2: 1.) H(+); 2.) propylene oxide / 2.) ethanol With sodium azide, methanesulfonic acid, hydrogen cation, methyloxirane in chloroform Georg, Gunda I.; Guan, Xiangming; Kant, Joydeep; Tetrahedron Letters; vol. 29; nb. 4; (1988); p. 403 - 406 View in Reaxys

OH O

NH 2

NH HO

Rx-ID: 3158598 View in Reaxys 87/105 Yield

Conditions & References With hydrogenchloride in tetrahydrofuran, water, T= 110 °C Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys

N O O–

NH 2

Ni 2+

N N–

Rx-ID: 3287037 View in Reaxys 88/105 Yield 80 %

Conditions & References With hydrogenchloride in ethanol, Time= 0.333333h, Heating 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

OH NH 2

aq.-ethanolic KOH Br

Rx-ID: 19115631 View in Reaxys 89/105

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Yield

Conditions & References Reaction Steps: 2 1: 1.) lithium diethylamide / 1.) THF, hexane, -78 deg C, 40 min; 2.) THF, hexane, -78 deg C up to 20 deg C within 2 h; r.t. overnight 2: 95 percent / FeCl3, SiO2 / aq. HCl / 3 h / Heating With lithium diethylamide, silica gel, iron(III) chloride in hydrogenchloride Seebach, Dieter; Fadel, Antoine; Helvetica Chimica Acta; vol. 68; (1985); p. 1243 - 1250 View in Reaxys Reaction Steps: 3 1: 1.) lithium diisopropylamide / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 5 h 2: H2 / Pd-C 3: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C With hydrogenchloride, hydrogen, lithium diisopropyl amide, palladium on activated charcoal in tetrahydrofuran, water Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys Reaction Steps: 4 1: 1.) lithium diisopropylamide / 1.) THF, 0 deg C, 15 min, 2.) THF, -78 deg C, 5 h 2: CF3COOH 3: Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 4: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C With hydrogenchloride, ammonia, lithium, trifluoroacetic acid, lithium diisopropyl amide in tetrahydrofuran, water, tert-butyl alcohol Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys

O NH 2

O N O OH

Rx-ID: 19503403 View in Reaxys 90/105 Yield

Conditions & References Reaction Steps: 2 1: Li/NH3 / tetrahydrofuran; 2-methyl-propan-2-ol 2: 6 N hydrochloric acid / tetrahydrofuran; H2O / 110 °C With hydrogenchloride, ammonia, lithium in tetrahydrofuran, water, tert-butyl alcohol Ojima; Qiu; Journal of the American Chemical Society; vol. 109; nb. 21; (1987); p. 6537 - 6538 View in Reaxys

OH NH 2

O N O O

Rx-ID: 3604966 View in Reaxys 91/105 Yield 95 %

Conditions & References With silica gel, iron(III) chloride in hydrogenchloride, Time= 3h, Heating Seebach, Dieter; Fadel, Antoine; Helvetica Chimica Acta; vol. 68; (1985); p. 1243 - 1250

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View in Reaxys

NH 2

O NH OH

Rx-ID: 2669965 View in Reaxys 92/105 Yield

Conditions & References With hydrogen, palladium on activated charcoal in methanol, Time= 2h, p= 206.9Torr Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340 View in Reaxys

H N

OH NH 2

Rx-ID: 21520164 View in Reaxys 93/105 Yield

Conditions & References Reaction Steps: 4 1: p-toluolsulfonic acid / 1,1,1-trichloro-ethane / 18 h / Heating 2: 1) K-hexamethyldisilazide / 1) THF-toluene, -78 deg C, 5 min, 2) warming up to rt. 3: 1N NaOH / methanol / Ambient temperature 4: H2 / 10percent Pd/C / methanol / 2 h / 206.9 Torr With sodium hydroxide, K-hexamethyldisilazide, hydrogen, toluene-4-sulfonic acid, palladium on activated charcoal in methanol, 1,1,1- trichloroethane Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340 View in Reaxys

Cl O

O N

NH 2

Rx-ID: 21548580 View in Reaxys 94/105 Yield

Conditions & References Reaction Steps: 3 1: 1) K-hexamethyldisilazide / 1) THF-toluene, -78 deg C, 5 min, 2) warming up to rt. 2: 1N NaOH / methanol / Ambient temperature 3: H2 / 10percent Pd/C / methanol / 2 h / 206.9 Torr With sodium hydroxide, K-hexamethyldisilazide, hydrogen, palladium on activated charcoal in methanol Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340 View in Reaxys

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OH NH 2

O N

Rx-ID: 21548702 View in Reaxys 95/105 Yield

Conditions & References Reaction Steps: 2 1: 1N NaOH / methanol / Ambient temperature 2: H2 / 10percent Pd/C / methanol / 2 h / 206.9 Torr With sodium hydroxide, hydrogen, palladium on activated charcoal in methanol Karady, Sandor; Amato, Joseph S.; Weinstock, Leonard M.; Tetrahedron Letters; vol. 25; nb. 39; (1984); p. 4337 - 4340 View in Reaxys

OH NH 2

O N

Rx-ID: 21548703 View in Reaxys 96/105 Yield

O NH 2

OH NH 2

Rx-ID: 2185812 View in Reaxys 97/105 Yield

Conditions & References With hydrogenchloride in water, Heating Anantharamaiah, G. M.; Roeske, Roger W.; Tetrahedron Letters; vol. 23; nb. 33; (1982); p. 3335 - 3336 View in Reaxys

O O O

OH NH 2

H 2N

Rx-ID: 21480740 View in Reaxys 98/105

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Yield

Conditions & References Reaction Steps: 2 1: α-chymotrypsin / H2O / 35 h / 37 °C / pH=5.0 2: aq. HCl / H2O / Heating With hydrogenchloride, α-chymotrypsin in water Anantharamaiah, G. M.; Roeske, Roger W.; Tetrahedron Letters; vol. 23; nb. 33; (1982); p. 3335 - 3336 View in Reaxys

-1

H O

F NH 2

(v4)

NH 2

B FF

O+

O HO

H 2N

Rx-ID: 2394246 View in Reaxys 99/105 Yield

Conditions & References Multistep reaction. Title compound not separated from byproducts Schoellkopf, Ulrich; Hartwig, Wolfgang; Groth, Ulrich; Westphalen, Karl-Otto; Liebigs Annalen der Chemie; nb. 4; (1981); p. 696 - 708 View in Reaxys

O F

OH NH 2

F O

Rx-ID: 1137933 View in Reaxys 100/105 Yield

Conditions & References With sodium hydroxide Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955 View in Reaxys

O F

OH NH 2

F F

Rx-ID: 22486668 View in Reaxys 101/105 Yield

Conditions & References Reaction Steps: 2 1: aq. NaOH / (enzymatic transformation) 2: aq. NaOH With sodium hydroxide Turk; Panse; Marshall; The Journal of organic chemistry; vol. 40; nb. 7; (1975); p. 953 - 955 View in Reaxys

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O NH 2

HO HN O

Rx-ID: 1143640 View in Reaxys 102/105 Yield

Conditions & References With hydrogenchloride, Heating Kobayashi,M. et al.; Chemical and Pharmaceutical Bulletin; vol. 20; (1972); p. 1898 - 1905 View in Reaxys With hydrogenchloride Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143 View in Reaxys Yamada,S.; Terashima,S.; Chemical and Pharmaceutical Bulletin; vol. 16; nb. 9; (1968); p. 1816 - 1828 View in Reaxys

NH 2

HN O

Rx-ID: 22790124 View in Reaxys 103/105 Yield

Conditions & References Reaction Steps: 4 1: Ac2O / 6 h / Heating 2: (i) Na, (ii) /BRN= 3952715/ 3: KOH 4: aq. HCl With hydrogenchloride, potassium hydroxide, acetic anhydride Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143 View in Reaxys

OH NH 2

N O O

Rx-ID: 22794416 View in Reaxys 104/105 Yield

Conditions & References Reaction Steps: 3 1: (i) Na, (ii) /BRN= 3952715/ 2: KOH 3: aq. HCl With hydrogenchloride, potassium hydroxide Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143 View in Reaxys

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O O N H

OH NH 2

Rx-ID: 22803322 View in Reaxys 105/105 Yield

Conditions & References Reaction Steps: 2 1: KOH 2: aq. HCl With hydrogenchloride, potassium hydroxide Terashima,S. et al.; Chemical and Pharmaceutical Bulletin; vol. 14; (1966); p. 1138 - 1143 View in Reaxys

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