methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate

Base Information

• Chemical Name: methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate
• CAS No.: 147745-25-3
• Molecular Formula: C₁₉H₂₆N₂O₆
• Molecular Weight: 378.425

Synonyms:methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate

Chemical Property of methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate

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Technology Process of methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate

There total 2 articles about methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate 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: 85.0%

2-amino-3-oxo-butyric acid methyl ester (68277-01-0) + N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) → methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate (147745-25-3)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -20 ℃;

DOI:10.1016/S0040-4039(02)01365-5

Reference yield:

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + (±)-2-amino-3-oxo-butyric acid methyl ester hydrochloride (41172-77-4) → methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate (147745-25-3)

Guidance literature:

With 4-methyl-morpholine; isobutyl chloroformate; Yield given. Multistep reaction; 1) THF, -20 deg C, 15 min, 2) THF, -20 deg C, 30 min;

DOI:10.1016/S0040-4039(00)60549-X

Reference yield: 84.0%

methyl 2-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanamido)-3-oxobutanoate (147745-25-3) → (S)-methyl 2-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)-5-methyloxazole-4-carboxylate (1257861-35-0)

Guidance literature:

With iodine; triethylamine; triphenylphosphine; In dichloromethane; at 20 ℃; for 16h;

DOI:10.1021/acs.orglett.7b01393

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

(±)-2-amino-3-oxo-butyric acid methyl ester hydrochloride

2-amino-3-oxo-butyric acid methyl ester

Downstream raw materials:

2-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-1,5-dimethyl-1H-imidazole-4-carboxylic acid methyl ester

2-(1-tert-butoxycarbonylamino-2-phenyl-ethyl)-1,5-dimethyl-1H-imidazole-4-carboxylic acid

(S)-methyl 2-(1-((tert-butoxycarbonyl)amino)-2-phenylethyl)-5-methyloxazole-4-carboxylate

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