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

Base Information

Chemical Name:(3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester
CAS No.:322729-62-4
Molecular Formula:C₂₄H₂₁N₃O₄
Molecular Weight:415.448
Hs Code.:

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

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

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

There total 7 articles about (3S)-2-oxo-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: 100.0%

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

: 322729-62-4
(3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Guidance literature:: With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; potassium bromide; In dichloromethane; water; at 0 ℃; for 0.5h;
DOI:10.1016/S0040-4020(00)00883-8

Reference yield:

: 37790-20-8
(E)-4-(phenyldiazenyl)benzoic acid

: 322729-62-4
(3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / EDCI; HOBT; DIEA / dimethylformamide; CH₂Cl₂ / 16 h / 20 °C

2: 100 percent / TEMPO; NaOCl/NaHCO₃; KBr / H₂O; CH₂Cl₂ / 0.5 h / 0 °C

With 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium bromide; In dichloromethane; water; N,N-dimethyl-formamide; 1: Condensation / 2: Oxidation;
DOI:10.1016/S0040-4020(00)00883-8

Reference yield:

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

: 322729-62-4
(3S)-2-oxo-4-phenyl-3-[[[4-(phenylazo)benzene]carbonyl]amino]butanoic acid methyl ester

Guidance literature:: Multi-step reaction with 6 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

6: 100 percent / TEMPO; NaOCl/NaHCO₃; KBr / H₂O; CH₂Cl₂ / 0.5 h / 0 °C

With dmap; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; zinc(II) tetrahydroborate; hydrogen bromide; sodium hydrogencarbonate; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; potassium bromide; In tetrahydrofuran; diethyl ether; dichloromethane; water; acetic acid; N,N-dimethyl-formamide; 1: Acylation / 2: Esterification / 3: Reduction / 4: amide cleavage / 5: Condensation / 6: Oxidation;
DOI:10.1016/S0040-4020(00)00883-8