Dicyclohexylcarbodiimide → HCID 131716561, compound

Participants

Reaction Steps

In 50 ml of DMF were added 3.43 g of 2-(2-formylamino1,3-thiazol-4-yl)-2-methoxyiminoacetic acid, 10.1 g of pivaloyloxymethyl 7-amino-3-[(2-methoxymethyl-5-methyl-s-triazolo[1,5-a]pyrimidin-7-yl)thiomethyl]-3-cephem-4-carboxylate and 2.76 g of 1-hydroxybenzotriazole and ice-cooled, and 3.71 g of DCC was added to the solution and the mixture was stirred for 1.5 hours under ice-cooling. After filtration of the reaction mixture, 20 ml of chloroform was added to the filtrate, and the mixture was added dropwise into 4 liters of ether. Precipitates were collected by filtration and dried to obtain a powder. To 1.57 ml of phosphorus oxychloride was added 80 ml of ice-cooled methanol, and the powder previously obtained was added thereto and the mixture was stirred for 1.5 hours under ice-cooling. After the mixture was condensed to a half, the residue was added dropwise to a mixed solution of 200 ml of water and 200 ml of ethyl acetate and the mixture was neutralized with addition of sodium hydrogencarbonate. An organic layer was separated, washed with water and then dried over anhydrous magnesium sulfate, followed by evaporation of a solvent to obtain an oily product. The oily product was purified through silica gel column chromatography. To the oily product obtained was added ether to powderize, and it was collected by filtration and dried to obtain 3.4 g of the title compound.

Provenance & Evidence