Acetonitrile → Methyl Acetate

Participants

Reaction Steps

A solution of 2.5 g of 3-(5-diphenylmethoxycarbonylfurfuryl)-7β-phenylacetylamino-ceph-2-em-4ξ-carboxylic acid diphenylmethyl ester in 10 ml of a 1:1-mixture of acetonitrile and isopropanol is treated at 0°-5° with 0.7 g of 3-chloroperbenzoic acid and stirred for 2 hours. The reaction product is worked up as usual (see Example 71) and the crude product is purified by column chromatography (silica gel; elution with a 4:1-mixture of methylene chloride and methyl acetate), to yield the colourless, foamy 3-(5-diphenylmethoxycarbonyl-furfuryl)-7β-phenylacetylamino-ceph-3-em-4-carboxylic acid diphenylmethyl ester 1-oxide; thin-layer chromatogram (silica gel); Rf = 0.43 (system: toluene/acetone 4:1) and Rf = 0.53 (system: toluene/ethyl acetate 4:1); ultraviolet absorption spectrum (in 95% aqueous ethanol): λmax = 269-273 mμ (ε = 21000).

Provenance & Evidence