Water → HCID 131720177, compound

Participants

Reaction Conditions

Reaction Steps

85 mg of N-chloroethyl pyrrolidine hydrochloride, 2 ml of methylene chloride and 210 μl of triethylamine were mixed together and 412 mg of diphenylmethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-mercapto-8-oxo-4-thia-1-azabicyclo[4,2,0]oct-2-en-2-carboxylate in 3 ml of methylene choride was added. The mixture was refluxed for 3 hours and after cooling to 20° C., the reaction mixture was poured into 10 ml of iced water. The mixture was stirred for 5 minutes, decanted and re-extracted with methylene chloride. The combined organic phases were dried and concentrated to dryness under reduced pressure. The residue was chromatographed on silica and eluted with a mixture of methylene chloride and acetone (1-1). After taking up again in isopropyl ether, 157 mg of syn isomer of racemic cis diphenylmethyl 7-[2-(2-tritylaminothiazol-4-yl)-2-methoxyimino-acetamido]-3-[(2-(1-pyrrolidinyl)-ethyl)-thio]-8-oxo-4-thia-1-azabicyclo [4,2,0]oct-2-en-2-carboxylate were obtained.

Provenance & Evidence