3-amino-4-oxo-heptanedioic acid 1-benzyl ester

Base Information

• Chemical Name: 3-amino-4-oxo-heptanedioic acid 1-benzyl ester
• CAS No.: 768395-72-8
• Molecular Formula: C₁₄H₁₇NO₅
• Molecular Weight: 279.293
• Mol file: 768395-72-8.mol

Synonyms:3-amino-4-oxo-heptanedioic acid 1-benzyl ester

Chemical Property of 3-amino-4-oxo-heptanedioic acid 1-benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-amino-4-oxo-heptanedioic acid 1-benzyl ester

There total 5 articles about 3-amino-4-oxo-heptanedioic acid 1-benzyl 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: 97.0%

benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate (768395-88-6) → 3-amino-4-oxo-heptanedioic acid 1-benzyl ester (768395-72-8)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/jm040780c

Reference yield:

dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate (768395-80-8) → 3-amino-4-oxo-heptanedioic acid 1-benzyl ester (768395-72-8)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 53 percent / lithium chloride; triethylamine / acetonitrile / 1 h / 0 °C

2.1: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

3.1: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

4.1: aq. Cs₂CO₃ / methanol / pH 8

4.2: 72 percent / dimethylformamide / 6 h / 20 °C

5.1: 97 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With dipyridinium dichromate; hydrogen; caesium carbonate; triethylamine; trifluoroacetic acid; lithium chloride; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Horner-Wadsworth-Emmons reaction;

DOI:10.1021/jm040780c

Reference yield:

tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate (768395-82-0) → 3-amino-4-oxo-heptanedioic acid 1-benzyl ester (768395-72-8)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 59 percent / H₂ / Pd/C / ethyl acetate / 3 h / 20 °C

2.1: 62 percent / pyridinium dichromate / dimethylformamide / 2.5 h

3.1: aq. Cs₂CO₃ / methanol / pH 8

3.2: 72 percent / dimethylformamide / 6 h / 20 °C

4.1: 97 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

With dipyridinium dichromate; hydrogen; caesium carbonate; trifluoroacetic acid; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm040780c

upstream raw materials:

benzyl (3R/S)-6-(tert-butoxycarbonyl)-3-[N-(tert-butoxycarbonyl)amino]-4-oxo-hexanoate

dimethyl [(3S)-3-[N-(tert-butoxycarbonyl)amino]-5-hydroxy-2-oxopentyl]phosphonate

tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-(E)-2-heptenoate

tert-butyl (5S)-5-[N-(tert-butoxycarbonyl)amino]-7-hydroxy-4-oxo-heptanoate