methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate

Base Information

• Chemical Name: methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate
• CAS No.: 148692-40-4
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 148692-40-4.mol

Synonyms:methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate

Chemical Property of methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate

There total 5 articles about methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate 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: 62.0%

methanol (67-56-1) + tert-butyl (S)-(4-cyano-3-oxo-1-phenyl-4-(triphenyl-λ5-phosphanylidene)butan-2-yl)carbamate → methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate (148692-40-4)

Guidance literature:

With 3,3-dimethyldioxirane; In acetone; at 20 ℃; for 0.0833333h;

DOI:10.1021/jo0015974

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate (148692-40-4)

Guidance literature:

Multi-step reaction with 2 steps

1: EDCI; DMAP / CH₂Cl₂ / 20 °C

2: 62 percent / dimethyldioxirane / acetone / 0.08 h / 20 °C

With dmap; 3,3-dimethyldioxirane; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; acetone;

DOI:10.1021/jo0015974

Reference yield:

N-(tert-butyloxycarbonyl)-(2RS,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester (820993-99-5) → methyl (S)-(t-butoxy carbonylamino)-2-oxo-4-phenylbutyrate (148692-40-4)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; Multistep reaction; 1.) CH₂Cl₂, -77 deg C, 20 min, 2.) CH₂Cl₂, -77 deg C, 10 min;

DOI:10.1021/jm00054a004

upstream raw materials:

N-(tert-butyloxycarbonyl)-(2RS,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

methanol

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

N-(tert-butyloxycarbonyl)-(2RS,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

N-(tert-butyloxycarbonyl)-(2S,3S)-3-amino-2-hydroxy-4-phenylbutanoic acid methyl ester

(S)-3-Amino-2-oxo-4-phenyl-butyric acid methyl ester; hydrochloride

Refernces

• 1、 Wong,Yu,Yuen,Yang. "Synthesis of α-keto esters and amides via oxidative cleavage of cyanoketophosphoranes by dimethyldioxirane". . p. 3606 - 3609. Retrieved 2007/10/03.