Dimethylformamide → HCID 131715761, compound

Participants

Reaction Conditions

Reaction Steps

6.35 ml (68 mmol) of phosphorus oxychloride was added to 20 ml of dry ethyl acetate. 5.28 ml (68 mmol) of N,N-dimethylformamide was dropwise added thereto at 0° C., and the mixture was stirred at the same temperature for 15 minutes. To this solution, 180 ml of dry methylene chloride was added. 25.2 g (57 mmol) of 2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetic acid (syn-isomer) was added thereto at 0° C., and the mixture was stirred for 30 minutes. Then, to this solution, 23.6 g (57 mmol) of benzhydryl 7-amino-3-chloromethyl-3-cephem-4-carboxylate was added, and the mixture was stirred at 0° C. for 2 hours. The reaction solution was adjusted to pH 7.0, and insoluble substances were filtered off. The filtrate was washed sequentially with 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 44.5 g (yield: 99%) of benzhydryl 3-chloromethyl-7-[2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-cephem-4-carboxylate (syn-isomer).

Provenance & Evidence