Hydrochloric Acid → HCID 178474913, compound

Participants

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-(1-diphenylmethoxycarbonylvinyloxyimino)acetamido]-3-(trityl-1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (910 mg: 0.723 mMol.) in a mixture of anisole (3 ml) and nitromethane (12 ml) at -40° C. is added a solution of aluminum chloride (0.77 g: 5.79 mMol.) in anisole (3 ml), and the mixture is stirred at -30° to -40° C. for 50 minutes. The reaction mixture is mixed with 1N-hydrochloric acid (5.8 ml), diluted with water, washed with ethyl acetate, and concentrated under reduced pressure to remove the remaining organic solvents. The resulting aqueous solution is subjected to chromatography over styrene divinylbenzene copolymer (methanol: water=4:1), and resulting powder is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(1-carboxyvinyloxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid (326 mg) as pale yellow white powder. Yield: 77%.

Provenance & Evidence