(6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Base Information

• Chemical Name: (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester
• CAS No.: 188534-21-6
• Molecular Formula: C₄₁H₄₃N₃O₁₀S
• Molecular Weight: 769.873

Synonyms:(6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

Chemical Property of (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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Technology Process of (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

There total 4 articles about (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ⁴-thia-1-aza-bicyclo[4.2.0]oct-2-ene-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: 91.7%

(E)-(2R,6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester (175917-53-0) → (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (188534-21-6)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; for 1h;

DOI:10.1021/jm950886v

Reference yield:

carbonic acid 4-aminophenyl ester tert-butyl ester (95932-39-1) → (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (188534-21-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 66.8 percent / Et₃N / CH₂Cl₂ / 0.5 h

2: 97 percent / Dowex 2 x 10, 50percent aq. NaOH / CH₂Cl₂ / 4 h / Ambient temperature

3: 1.) PPh₃ / 1.) benzene, reflux, 120 h, 2.) 1,2-dichloroethane, 1,2-epoxybutane, reflux, 3.5 h

4: 91.7 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h

With sodium hydroxide; Dowex 2 x 10; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In dichloromethane;

DOI:10.1021/jm950886v

Reference yield:

carbonic acid (RS)-4-(3-bromo-2-oxopyrrolidin-1-yl)phenyl ester tert-butyl ester (175917-51-8) → (6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-5,8-dioxo-5λ4-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester (188534-21-6)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) PPh₃ / 1.) benzene, reflux, 120 h, 2.) 1,2-dichloroethane, 1,2-epoxybutane, reflux, 3.5 h

2: 91.7 percent / m-chloroperbenzoic acid / CH₂Cl₂ / 1 h

With 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; In dichloromethane;

DOI:10.1021/jm950886v

upstream raw materials:

(E)-(2R,6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-3-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-3-ene-2-carboxylic acid benzhydryl ester

carbonic acid 4-aminophenyl ester tert-butyl ester

carbonic acid (RS)-4-(3-bromo-2-oxopyrrolidin-1-yl)phenyl ester tert-butyl ester

carbonic acid (RS)-4-<(2,4-dibromobutyryl)amino>phenyl ester tert-butyl ester

Downstream raw materials:

(6R,7R)-7-tert-Butoxycarbonylamino-3-[1-(4-tert-butoxycarbonyloxy-phenyl)-2-oxo-pyrrolidin-(3E)-ylidenemethyl]-8-oxo-5-thia-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzhydryl ester

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