(2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester
• CAS No.: 189286-10-0
• Molecular Formula: C₃₀H₃₄N₂O₈S
• Molecular Weight: 582.675
• Mol file: 189286-10-0.mol

Synonyms:

Chemical Property of (2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

There total 2 articles about (2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl 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:

(2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester (182750-66-9) → (2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (189286-10-0)

Guidance literature:

Multi-step reaction with 2 steps

1: oxalyl chloride / dimethylformamide

2: triethylamine

With oxalyl dichloride; triethylamine; In N,N-dimethyl-formamide; 1: Chlorination / 2: Substitution;

DOI:10.7164/antibiotics.50.276

Reference yield:

proline tert-butyl ester (2812-46-6) + (2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (1026477-53-1) → (2S,3R,5R)-3-((S)-2-tert-Butoxycarbonyl-pyrrolidine-1-carbonyl)-3-methyl-4,4,7-trioxo-4λ6-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester (189286-10-0)

Guidance literature:

With triethylamine;

DOI:10.7164/antibiotics.50.276

upstream raw materials:

proline tert-butyl ester

(2S,3R,5R)-3-Chlorocarbonyl-3-methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2-carboxylic acid benzhydryl ester

(2S,3R,5R)-3-Methyl-4,4,7-trioxo-4λ⁶-thia-1-aza-bicyclo[3.2.0]heptane-2,3-dicarboxylic acid 2-benzhydryl ester