3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester

Base Information

• Chemical Name: 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester
• CAS No.: 142165-88-6
• Molecular Formula: C₂₀H₂₈N₂O₇
• Molecular Weight: 408.452

Synonyms:3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester

Chemical Property of 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester

Chemical Property:

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Technology Process of 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester

There total 3 articles about 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl 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: 69.0%

3-aminobenzoic acid ethyl ester (582-33-2) + N-tert-butoxycarbonylglutamic acid methyl ester (72086-72-7) → 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester (142165-88-6)

Guidance literature:

With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; Ambient temperature;

DOI:10.1248/cpb.45.1146

Reference yield:

Boc-Glu(OBzl)-OH (13574-13-5) → 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester (142165-88-6)

Guidance literature:

Multi-step reaction with 3 steps

1: diethyl ether

2: H₂ / 10percent Pd/C / methanol / 15 h / Ambient temperature

3: diethyl phosphorocyanidate, Et₃N / dimethylformamide / 2 h / Ambient temperature

With diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1248/cpb.44.1498

Reference yield:

Nα-tert-butyloxycarbonyl-γ-benzyloxycarbonyl-L-glutamic acid methyl ester (59279-58-2) → 3-((S)-4-tert-Butoxycarbonylamino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester (142165-88-6)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂ / 10percent Pd/C / methanol / 15 h / Ambient temperature

2: diethyl phosphorocyanidate, Et₃N / dimethylformamide / 2 h / Ambient temperature

With diethyl cyanophosphonate; hydrogen; triethylamine; palladium on activated charcoal; In methanol; N,N-dimethyl-formamide;

DOI:10.1248/cpb.44.1498

upstream raw materials:

3-aminobenzoic acid ethyl ester

N-tert-butoxycarbonylglutamic acid methyl ester

Boc-Glu(OBzl)-OH

N^α-tert-butyloxycarbonyl-γ-benzyloxycarbonyl-L-glutamic acid methyl ester

Downstream raw materials:

3-((S)-4-Amino-4-methoxycarbonyl-butyrylamino)-benzoic acid ethyl ester

3-{(S)-4-[(2,3-Dihydro-1H-indole-5-carbonyl)-amino]-4-methoxycarbonyl-butyrylamino}-benzoic acid ethyl ester

methyl N^α-[(1-benzyloxycarbonylindolin-5-yl)carbonyl]-N^δ-(3-ethoxycarbonylphenyl)-L-glutaminate

methyl N^α-{1-[(2,4-diaminopteridin-6-yl)methyl]indolin-5-ylcarbonyl}-N^δ-(3-ethoxycarbonylphenyl)-L-glutaminate

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