(2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester

Base Information

• Chemical Name: (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester
• CAS No.: 172479-51-5
• Molecular Formula: C₁₆H₂₁NO₅
• Molecular Weight: 307.346
• Mol file: 172479-51-5.mol

Synonyms:(2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester

Chemical Property of (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester

There total 17 articles about (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric 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: 38.0%

methanol (67-56-1) + tert-butyl (S,Z)-(5-oxo-1,5-diphenylpent-1-en-3-yl)carbamate → (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester (172479-51-5)

Guidance literature:

With ozone; sodium hydroxide; In dichloromethane; at -78 ℃;

DOI:10.1039/c7cc04674j

Reference yield:

N-(tert-butoxycarbonyl)glycine methyl ester (31954-27-5) → (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester (172479-51-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: N-bromosuccinimide

2.1: piperidinomethylpolystyrene / CH₂Cl₂ / 0.17 h / 20 °C

3.1: Cu(OTf)2; (R,R)-(1-naphthyl-CH₂NHCHPh)2 / CH₂Cl₂ / 1 h / -20 °C

3.2: aq. HCl / tetrahydrofuran / 2 h / 20 °C

With (1R,2R)-N,N’-bis(naphthalen-1-ylmethyl)-1,2-diphenylethane-1,2-diamine; N-Bromosuccinimide; piperidinomethylpolystyrene; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; 3.1: Mannich-type reaction;

DOI:10.1021/ol034717d

Reference yield:

1-styrenyloxytrimethylsilane (13735-81-4) + [(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester (81357-15-5) → (2S)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester (172479-51-5) + (2R)-2-tert-butoxycarbonylamino-4-oxo-4-phenylbutyric acid methyl ester

Guidance literature:

1-styrenyloxytrimethylsilane; [(E)-tert-Butoxycarbonylimino]-acetic acid methyl ester; With (1R,2R)-N,N’-bis(naphthalen-1-ylmethyl)-1,2-diphenylethane-1,2-diamine; copper(II) bis(trifluoromethanesulfonate); In dichloromethane; at -20 ℃; for 1h;

With hydrogenchloride; In tetrahydrofuran; at 20 ℃; for 2h; Title compound not separated from byproducts;

DOI:10.1021/ol034717d

upstream raw materials:

iodobenzene

carbon monoxide

N-(tert-butoxycarbonyl)-L-3-iodoalanine methyl ester

1-styrenyloxytrimethylsilane

Downstream raw materials:

S-2-amino-4-carbonyl-4-phenylbutyric acid hydrochloride

Refernces

• 1、 Barfoot, Christopher W.,Harvey, Joanne E.,Kenworthy, Martin N.,Kilburn, John Paul,Ahmed, Mahmood,Taylor, Richard J.K.. "Highly functionalised organolithium and organoboron reagents for the preparation of enantiomerically pure α-amino acids". . p. 3403 - 3417. Retrieved 2007/10/03.
• 2、 Nakamura, Yoshitaka,Matsubara, Ryosuke,Kiyohara, Hiroshi,Kobayashi, Shu. "Catalytic, asymmetric Mannich-type reactions of α-imino esters bearing readily removable substituents on nitrogen". . p. 2481 - 2484. Retrieved 2007/10/03.