Triethylamine → HCID 131714792, compound

Participants

Reaction Steps

420 mg of phosphorus pentachloride was dissolved in 70 ml of chloroform and the mixture was cooled to -25° to -30° C. 1.51 g of 2-(2-tritylaminothiazol-4-yl)-2-((N-tritylpyrazol-3-yl)methoxyimino)acetic acid was added to the mixture and the resulting mixture was stirred for 30 minutes at the same temperature. 0.5 ml of triethylamine was added to the mixture and, after 3 minutes, a mixture of 810 mg of tertiary butyl 7β-amino-3-bromomethyl-3-cephem-4-carboxylate 1-oxide hydrochloride, 0.28 ml of triethylamine and methylene chloride was added to the mixture. The resulting mixture was stirred for 40 minutes at the same temperature. 50 ml of chloroform cooled in an ice-bath was added to the reaction mixture and the mixture was washed with water, a 3% aqueous solution of sodium bicarbonate and SSC and dried with sodium sulfate and then concentrated to dryness. The residue was purified by silica gel column chromatography using chloroform and nextly a mixture of chloroform and ethyl acetate (4:1 by volume) as an eluent solvent to give 1.92 g of tertiary butyl 7β-(2-(2-tritylaminothiazol-4-yl)-2-((N-tritylpyrazol-3-yl)methoxyimino)acetamido)-3-bromomethyl-3-cephem-4-carboxylate 1-oxide (syn isomer).

Provenance & Evidence