2-Azetidinecarboxylic acid, 4-oxo-1-[[[(1R)-1-phenylethyl]amino]carbonyl]-2-(phenylmethyl)-, 1,1-dimethylethyl ester, (2S)-

Base Information

• Chemical Name: 2-Azetidinecarboxylic acid, 4-oxo-1-[[[(1R)-1-phenylethyl]amino]carbonyl]-2-(phenylmethyl)-, 1,1-dimethylethyl ester, (2S)-
• CAS No.: 709015-06-5
• Molecular Formula: C24H28N2O4
• Molecular Weight: 408.497
• Mol file: 709015-06-5.mol

Synonyms:

Chemical Property of 2-Azetidinecarboxylic acid, 4-oxo-1-[[[(1R)-1-phenylethyl]amino]carbonyl]-2-(phenylmethyl)-, 1,1-dimethylethyl ester, (2S)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-Azetidinecarboxylic acid, 4-oxo-1-[[[(1R)-1-phenylethyl]amino]carbonyl]-2-(phenylmethyl)-, 1,1-dimethylethyl ester, (2S)-

There total 1 articles about 2-Azetidinecarboxylic acid, 4-oxo-1-[[[(1R)-1-phenylethyl]amino]carbonyl]-2-(phenylmethyl)-, 1,1-dimethylethyl ester, (2S)- 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: 50.0%

(1R)-1-phenylethyl isocyanate (33375-06-3) + 4-benzyl-4-tert-butoxycarbonyl-2-azetidinone (344765-43-1) → (S)-2-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidine-2-carboxylic acid tert-butyl ester (709015-06-5) + (R)-2-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidine-2-carboxylic acid tert-butyl ester (709015-08-7)

Guidance literature:

With caesium carbonate; In tetrahydrofuran; at 20 ℃;

DOI:10.1021/jm0492812

Reference yield: 90.0%

(S)-2-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidine-2-carboxylic acid tert-butyl ester (709015-06-5) → (S)-2-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidine-2-carboxylic acid (709015-10-1)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; for 2h;

DOI:10.1021/jm0492812

Reference yield:

(S)-2-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidine-2-carboxylic acid tert-butyl ester (709015-06-5) → (4S,1'R,1''S)-1-[(1'-phenyl)ethyl]aminocarbonyl-4-[(1''-methoxycarbonyl)ethyl]aminocarbonyl-4-benzyl-2-azetidinone

Guidance literature:

Multi-step reaction with 2 steps

1: 90 percent / TFA / CH₂Cl₂ / 2 h

2: 81 percent / BOP; TEA / tetrahydrofuran / 20 °C

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane;

DOI:10.1021/jm0492812

upstream raw materials:

(1R)-1-phenylethyl isocyanate

4-benzyl-4-tert-butoxycarbonyl-2-azetidinone

Downstream raw materials:

(S)-2-Benzyl-4-oxo-1-((R)-1-phenyl-ethylcarbamoyl)-azetidine-2-carboxylic acid