Hydrochloric Acid → HCID 178508517, compound

Participants

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetyl]amino-3-(1,2,3-thiadiazol-5-yl) thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (1.21 g: 1.16 mMol.) in a mixture of anisole (4 ml) and nitromethane (16 ml) cooling at -30° to -40° C. is added a solution of aluminum chloride (1.23 g: 9.25 mMol.) in anisole (4 ml), and the mixture is stirred at -30° to -40° C. for 50 minutes. To the reaction mixture is added 1N-hydrochloric acid (10 ml), diluted with water, and washed with ethyl acetate. The aqueous layer is concentrated to remove the organic solvents, purified by styrene-divinylbenzene copolymer chromatography (methanol: water=4:1) and the resulting powder is washed with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetyl]amino-3-(1,2,3-thiadiazol-5-yl)thiomethylthio-3-cephem-4-carboxylic acid as yellow powder (440 mg). Yield 71%.

Provenance & Evidence