N,N-Dimethylaniline → HCID 131715766, compound

Participants

Reaction Conditions

Reaction Steps

28 g (41 mmol) of 2-(1-benzhydryloxycarbonyl-1-methylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetic acid (syn-isomer) and 17 g (41 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate, were dissolved in 300 ml of dry methylene chloride, and 15.6 ml (123 mmol) of N,N-dimethylaniline was added thereto. The mixture was cooled to -10° C., and 4 ml (43 mmol) of phosphorus oxychloride was dropwise added thereto. The reaction solution was stirred at room temperature for 2.5 hours, and then concentrated under reduced pressure. The residue was extracted with ethyl acetate. The organic layer was washed sequentially with 1N hydrochloric acid, a 5% sodium hydrogen carbonate aqueous solution and a saturated sodium chloride aqueous solution, then dried over anhydrous sodium sulfate and concentrated under reduced pressure to obtain 36 g (yield: 81%) of benzhydryl 3-chloromethyl-7-[2-(1-benzhydryloxycarbonyl-1-methylethoxyimino)-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (syn-isomer).

Provenance & Evidence