5-Oxa-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid, 3-(chloroMethyl)-7- (4-Met

Base Information

• Chemical Name: 5-Oxa-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid, 3-(chloroMethyl)-7- (4-Met
• CAS No.: 91177-27-4
• Molecular Formula: C29 H25 Cl N2 O5
• Molecular Weight: 516.981
• Mol file: 91177-27-4.mol

Synonyms:5-Oxa-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid, 3-(chloromethyl)-7-[(4-methylbenzoyl)amino]-8-oxo-, diphenylmethyl ester, (6R-cis)- (9CI);

Chemical Property of 5-Oxa-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid, 3-(chloroMethyl)-7- (4-Met

Chemical Property:

• PSA: 84.94000
• LogP: 4.44640

Purity/Quality:

99%, ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Oxa-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid, 3-(chloroMethyl)-7- (4-Met

There total 10 articles about 5-Oxa-1-azabicyclo 4.2.0 oct-2-ene-2-carboxylic acid, 3-(chloroMethyl)-7- (4-Met 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:

C35H31ClN2O5S → 7-(N-4-methylbenzamide)-3-(chloromethyl)-8-oxo-5-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (91177-27-4)

Guidance literature:

C₃₅H₃₁ClN₂O₅S; With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 - 10 ℃; for 2.5h;

With sodium thiosulfate; In dichloromethane; water; at 0 - 10 ℃; for 4h;

Reference yield:

C29H26Cl2N2O5 → 7-(N-4-methylbenzamide)-3-(chloromethyl)-8-oxo-5-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (91177-27-4)

Guidance literature:

With methanol; at 0 - 5 ℃; for 5h; Reagent/catalyst;

Reference yield:

6β-(4-toluamido)penicillanic acid (17028-66-9) → 7-(N-4-methylbenzamide)-3-(chloromethyl)-8-oxo-5-oxo-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid diphenylmethyl ester (91177-27-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: pyridine; methanesulfonyl chloride / -5 - 10 °C

2.1: sodium tungstate; dihydrogen peroxide / 0 °C

3.1: chloro-trimethyl-silane; triethylamine / 10 °C

4.1: triphenylphosphine / ethyl acetate / 78 °C

5.1: chlorine; sodium hydrogencarbonate / water; ethyl acetate / 20 - 25 °C

5.2: 25 °C

6.1: pyridine; chlorine / dichloromethane

7.1: diethylamine / -20 °C

With pyridine; sodium tungstate; chloro-trimethyl-silane; dihydrogen peroxide; chlorine; sodium hydrogencarbonate; methanesulfonyl chloride; diethylamine; triethylamine; triphenylphosphine; In dichloromethane; water; ethyl acetate;

DOI:10.1016/j.cclet.2012.01.014

upstream raw materials:

6β-(4-toluamido)penicillanic acid

C₂₉H₂₈N₂O₅S

C₂₉H₂₆N₂O₄

diphenylmethyl (2R,6R,7R)-3-methylene-7-[(4-methylbenzoyl)amino]-8-oxo-5-oxa-1-azabicyclo[4.2.0]octane-2-carboxylate

Downstream raw materials:

C₁₇H₁₈F₂N₃O₆S⁽¹⁺⁾*I^(1-)

(6R,7R)-benzhydryl (7-(2-difluoromethylthio)acetamido)-3-(chloromethyl)-7-methoxy-8-oxo-5-oxa-1-aza-bicyclo[4,2,0]oct-2-ene-2-carboxylate

C₃₀H₂₆Cl₂N₂O₆S

C₃₀H₂₅Cl₃N₂O₆S