Oxalyl chloride → HCID 20294440, compound

Participants

Reaction Steps

0.59 g of sodium (3-benzoyloxyisoxazol-5-yl)acetate was suspended in 5 ml of methylene chloride, and 0.37 ml of oxalyl chloride were then added, with ice-cooling. After adding one drop of N,N-dimethylformamide, the mixture was stirred for 30 minutes. The solvent was then distilled off under reduced pressure to give (3-benzoyloxyisoxazol-5-yl)acetyl chloride, which was then dissolved in 5 ml of methylene chloride. This solution was added dropwise to a solution of 685 mg of benzhydryl 3-acetoxymethyl-7β-amino-7α-methoxy-3-cephem-4-carboxylate and 325 mg of N,N-diethylaniline in 5 ml of methylene chloride, maintaining the internal temperature at about -10° C. After stirring the mixture at a temperature between -10° C. and -5° C. for 45 minutes, the reaction mixture was evaporated to dryness under reduced pressure and the residue was adsorbed on a silica gel preparative thin layer chromatograph and developed by a 2:1 by volume mixture of benzene and ethyl acetate. The portion having an Rf value of 0.54 was extracted to give 660 mg (64.7%) of the benzhydryl ester of the desired Compound No. 4.

Provenance & Evidence