(2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Base Information

Chemical Name:(2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester
CAS No.:322729-60-2
Molecular Formula:C₂₄H₂₃N₃O₄
Molecular Weight:417.464
Hs Code.:

Synonyms:(2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

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Chemical Property of (2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

There total 4 articles about (2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 1161-13-3
N-Cbz-L-Phe

: 322729-60-2
(2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 78 percent / EDCI; DMAP / CH₂Cl₂ / 20 h / 20 °C

2: 77 percent / O₃ / CH₂Cl₂ / 0.25 h / -78 °C

3: 44 percent / Zn(BH₄)2 / tetrahydrofuran; diethyl ether / 2 h / -78 °C

4: 86 percent / HBr / acetic acid / 0.33 h / 20 °C

5: 89 percent / EDCI; HOBT; DIEA / dimethylformamide; CH₂Cl₂ / 16 h / 20 °C

With dmap; zinc(II) tetrahydroborate; hydrogen bromide; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: Acylation / 2: Esterification / 3: Reduction / 4: amide cleavage / 5: Condensation;
DOI:10.1016/S0040-4020(00)00883-8

Reference yield:

: 126015-22-3
(2R,3S)-3-[[(benzyloxy)carbonyl]amino]-2-hydroxy-4-phenylbutanoic acid methyl ester

: 322729-60-2
(2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 86 percent / HBr / acetic acid / 0.33 h / 20 °C

2: 89 percent / EDCI; HOBT; DIEA / dimethylformamide; CH₂Cl₂ / 16 h / 20 °C

With hydrogen bromide; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: amide cleavage / 2: Condensation;
DOI:10.1016/S0040-4020(00)00883-8

Reference yield:

: 214122-05-1
(4S)-4-[[(benzyloxy)carbonyl]amino]-3-oxo-5-phenyl-2-triphenylphosphoranylidene-pentanenitrile

: 322729-60-2
(2R,3S)-2-hydroxy-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 77 percent / O₃ / CH₂Cl₂ / 0.25 h / -78 °C

2: 44 percent / Zn(BH₄)2 / tetrahydrofuran; diethyl ether / 2 h / -78 °C

3: 86 percent / HBr / acetic acid / 0.33 h / 20 °C

4: 89 percent / EDCI; HOBT; DIEA / dimethylformamide; CH₂Cl₂ / 16 h / 20 °C

With zinc(II) tetrahydroborate; hydrogen bromide; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetic acid; N,N-dimethyl-formamide; 1: Esterification / 2: Reduction / 3: amide cleavage / 4: Condensation;
DOI:10.1016/S0040-4020(00)00883-8