Aluminum(III) Chloride → HCID 178508519, compound

Participants

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetyl]amino-3-(5-tetrazolyl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (942 mg: containing ca. 10% of byproduct) in a mixture of anisole (3 ml) and nitromethane (12 ml) cooling at -30° to -40° C. is added a solution of aluminum chloride (980 mg: 7.37 mMol.) in anisole (3 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is diluted with 1N-hydrochloric acid (7.5 ml) and water, washed with ethyl acetate, concentrated under reduced pressure to remove the organic solvents, and subjected to styrene-divinylbenzene copolymer chromatography (methanol: water=2:3). The resulting powder is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetyl]amino-3-(tetrazol-5-yl)thiomethylthio-3-cephem-4-carboxylic acid as pale yellow powder (289 mg). Yield: 28% (from 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetyl]amino-3-methanesulfonyloxy-3-cephem-4-carboxylic acid diphenylmethyl ester).

Provenance & Evidence