Hydrochloric Acid → HCID 131714763, compound

Participants

Reaction Steps

Methylene chloride (15 ml) was added to a Vilsmeier reagent, which was prepared by phosphoryl chloride (0.75 g) and N,N-dimethylformamide (0.75 ml) in a conventional manner. To this mixture was added 2-(4-formamidopyrimidin-2-yl)-2-phenoxyiminoacetic acid (syn isomer) (1.0 g) at -20° C., followed by stirring at -15° to -13° C. for half an hour. To this solution was added a solution of 7-amino-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (1.27 g) and trimethylsilylacetamide (4.6 g) in methylene chloride (14 ml) at -20° C. with stirring, and the stirring was continued at -15° to -13° C. for half an hour and at ambient temperature for additional half an hour. The reaction mixture was evaporated to give a residue, to which ethyl acetate and then an aqueous solution of sodium bicarbonate were added. To the separated aqueous solution was added ethyl acetate and then adjusted to pH 1 to 2 with hydrochloric acid. After addition of a small amount of acetone, the organic layer was separated, washed with water and an aqueous solution of sodium chloride, dried over magnesium sulfate, and then evaporated. The residue was pulverized with diethyl ether to give 7-[2-(4-formamidopyrimidin-2-yl)-2-phenoxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethyl)-3-cephem-4-carboxylic acid (syn isomer) (1.45 g).

Provenance & Evidence