m-Chloroperbenzoic acid → HCID 68133873, compound

Participants

Reaction Steps

A solution of 2.0 g of 3-(5-fluor-2-hydroxy-benzyl)7β-phenylacetylamino-ceph-2-em-4ξ-carboxylic acid in 10 ml of isopropanol is treated at 0°-5° in small amounts with 1.2 g of 3-chloro-perbenzoic acid and stirred for 2 hours. The reaction mixture is concentrated to half-volume and diluted with 10 ml of diethyl ether. The crystalline precipitate that forms is filtered off and recrystallised from methyl acetate to yield the 3-(5-fluoro-2-hydroxy-benzyl)-7-phenylacetylamino-ceph-3-em-4-carboxylic acid 1-oxide, which melts at 183°-185°; thin-layer chromatogram (silica gel) Rf = 0.48 (system: n-butanol/acetic acid/water 75:7.5:21), Rf = 0.64 (system: n-butanol/ethanol/water 40:10:50) and Rf = 0.77 (system: chloroform/methanol 1:1).

Provenance & Evidence