Methanesulfonyl chloride → HCID 178500988, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 531 mg (0.92 mM) of 2-(2-tritylaminothiazol-4-yl)-2-[(Z)-2,4-dimethoxybenzyloxyimino]acetic acid in 10 ml of N,N-dimethylformamide was added 124 mg (0.96 mM) of diisopropylethylamine. To the cooled (-50° C.) mixture was added 105 mg (0.92 mm) of methanesulfonyl chloride, and the mixture was stirred for 30 minutes. Then, 200 mg (0.46 mM) of 4-methoxybenzyl 7β-amino-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate and 60 mg (0.46 mM) of diisopropylethylamine were added at the same temperature, and the mixture was stirred for 30 minutes. After the reaction, 30 ml of water was added, the mixture was extracted with 50 ml of ethyl acetate, and the extract was washed with 30 ml of a saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was chromatographed on silica gel column (eluent; ethyl acetate:benzene=1:4) to give 270 mg of 4-methoxybenzyl 7β-{2-(2-tritylaminothiazol-4-yl)-2-[(Z)-2,4-dimethoxybenzyloxyimino]acetamido}-3-[(Z)-2-methoxycarbonylvinylthio]-3-cephem-4-carboxylate.

Provenance & Evidence