Ethanol → HCID 10075720, compound

Participants

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (535 mg: 0.51 mMol.) in a mixture of anisole (1 ml) and nitromethane (4 ml) is added a solution of aluminum chloride (0.61 g: 4.6 mMol.) in anisole (2 ml) at -30° C. and the mixture is stirred for 40 minutes. The reaction mixture is mixed with ethanol (2 ml), stirred for 5 minutes at the same temperature, diluted with 1N-hydrochloric acid (6 ml) and water (200 ml), and washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove the organic solvents and passed through a styrene-divinylbenzene copolymer column. The adsorbed material is eluted with a methanol-water (4:1) mixture. The eluate is concentrated to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(1,3,4-thiadiazol-2-ylthiomethylthio)-3-cephem-4-carboxylic acid as pale yellow solid (201 mg). Yield: 74%.

Provenance & Evidence