Phosphorus pentachloride → HCID 131714793, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of methylene chloride and 209 mg of phosphorus pentachloride was cooled to -10° C. 752 mg of 2-(2-tritylaminothiazol-4-yl)-2-((N-tritylimidazol-4-yl)methoxyimino)acetic acid was added to the mixture and the mixture was stirred for 10 minutes at the same temperature. 0.25 ml of triethylamine was added thereto and after 5 minutes a mixture of methylene chloride, 401 mg of tertiary butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrochloride and 0.14 ml of triethylamine was added to the mixture. The resulting mixture was stirred for 30 minutes at the same temperature. A 5% aqueous solution of sodium bicarbonate was added to the reaction mixture and the organic solvent layer was washed with a diluted aqueous solution of citric acid and SSC and dried with sodium sulfate and then concentrated to dryness to give 1.0 g tertiary butyl 7β-(2-(2-tritylaminothiazol-4-yl)-2-((N-tritylimidazol-4-yl)methoxyimino)acetamido)-3-bromomethyl-3-cephem-4-carboxylate 1-oxide (syn isomer).

Provenance & Evidence