Water → HCID 131712606, compound

Participants

Reaction Steps

A solution of iodomethyl hexanoate (1.58 g.) in dimethylformamide (3 ml.) was added at a time under ice-cooling to a stirred solution of sodium 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (3.0 g.) in dimethylformamide (15 ml.). The mixture was stirred for 10 minutes at the same temperature and poured into a mixture of water (50 ml.) and ethyl acetate (100 ml.). The aqueous layer was separated and extracted twice with ethyl acetate (50 ml.). The combined ethyl acetate layer was filtered and the filtrate was washed three times with an aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo to a volume of 20 ml. to give precipitates, which were collected by filtration, washed with ethyl acetate (10 ml.) and dried to give hexanoyloxymethyl 7-[2-methoxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-(1,3,4-thiadiazol-2-yl)thiomethyl-3-cephem-4-carboxylate (syn isomer) (2.1 g.).

Provenance & Evidence