Hydrochloric Acid → HCID 88659219, compound

Participants

Reaction Conditions

Reaction Steps

5 g of 3-acetoxymethyl-7-[2-(2-chloroacetamidothiazol-4-yl)-2-(Z)-methoxyiminoacetamido]-3-cephem-4-carboxylic acid and 800 mg of sodium hydrogen carbonate were dissolved in 50 ml of 70% v/v aqueous methanol. 75 g of anhydrous calcium chloride were added to the solution, and the mixture was stirred at 70° C. for 1 hour. The mixture was then diluted with 100 ml of ice-water, acidified by the addition of 1 ml of concentrated hydrochloric acid, and extracted three times, each time with 100 ml of ethyl acetate. The extracts were combined and the combined extracts were extracted three times, each time with 50 ml of a 10% w/v aqueous solution of dipotassium phosphate. The extracts were combined and the combined extracts were washed with a small amount of ethyl acetate, acidified with a saturated aqueous solution of potassium hydrogen sulphate, and extracted twice with 100 ml portions of ethyl acetate and then once with 50 ml of ethyl acetate. The extracts were combined and the combined extracts were washed with an aqueous solution of sodium chloride, dehydrated over anhydrous magnesium sulphate and concentrated by evaporation under reduced pressure. When the volume of the mixture had reduced to about 50 ml, the evaporation was stopped, as crystals began to precipitate. The concentrate was first heated to redissolve the crystals and then ice-cooled and allowed to stand for 3 hours. The resulting crystals were collected by filtration, washed with ethyl acetate and dried, to give 3.01 g (yield 63.5%) of the title compound.

Provenance & Evidence