Hydrochloric Acid → HCID 178491515, compound

Participants

Reaction Conditions

Reaction Steps

After 1.0 g (1.6 mmol) of (Z)-2-(2-tritylaminothiazol-4-yl)-[[(tert-butoxycarbonyl)(3-pyridyl)methoxy]imino]acetic acid and 0.37 g (1.77 mmol) of phosphorus pentachloride were added to 25 ml of dichloromethane, the mixture was stirred at 5° C. for 30 minutes. The resulting solution was dropwise added to a solution containing 0.65 g (1.6 mmol) of p-methoxybenzyl 7-amino-3-chloromethyl-3-cephem-4-carboxylate hydrochloride and 1.3 ml of pyridine in 30 ml of dichloromethane. After stirring for an hour below -20° C., the solution was cooled to -40° C. After adding 50 ml of 1N hydrochloric acid, the temperature was reverted to room temperature. The dichloromethane layer was taken out, washed with saturated sodium chloride aqueous solution and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was subjected to silica gel column chromatography. The column was eluted with dichloromethane-methanol (10:1) to give 0.90 g (57.7%) of p-methoxybenzyl 7β-[(Z)-2-(2-tritylamino-4-thiazolyl)-2-[[(R S)-(tert-butoxycarbonyl)(3-pyridyl)methoxy]imino]acetamido]-3-chloromethyl-3-cephem-4-carboxylate.

Provenance & Evidence