m-Chloroperbenzoic acid → HCID 86739902, compound

Participants

Reaction Steps

A solution of 2-benzhydryloxycarbonyl-3-(2-chloroacetamido-thiazol-5-yl)-7-(3,4-dichlorophenylthio)-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene (2 g) in methylene chloride (50 cc) is cooled to 0° C. and treated with an 85% strength solution of meta-chloroperbenzoic acid (0.45 g) in methylene chloride (10 cc). After 30 minutes at a temperature of between 0° and 5° C., the reaction mixture is diluted with methylene chloride (100 cc) and a saturated sodium bicarbonate solution (100 cc) is added. The solid which precipitates is filtered off and taken up in methylene chloride (200 cc). The decanted organic phase is added to this solution, after having been washed with water (100 cc) and then with a saturated sodium chloride solution (100 cc) and dried over sodium sulphate, and the mixture is then concentrated under reduced pressure to a residual volume of 10 cc. The solid is filtered off and washed with ethyl acetate (20 cc) and then with ethyl ether (20 cc). 2-Benzhydryloxycarbonyl-3-(2-chloroacetamido-thiazol-5-yl)-7-(3,4-dichlorophenylthio)-acetamido-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-5-oxide (1.48 g) is obtained in the form of a cream solid.

Provenance & Evidence