Ethanol → HCID 10415042, compound

Participants

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (388 mg: 0.368 mMol.) in a mixture of anisole (1 ml) and nitromethane (4 ml) at -30° C. is added a solution of aluminum chloride (0.45 g: 9.2 equivalents: 3.4 mMol.) in anisole (1.5 ml), 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, and diluted with 1N-hydrochloric acid (6 ml) and water (200 ml). The aqueous layer is taken, washed with ethyl acetate, concentrated under reduced pressure to remove the organic solvents, and passed through a column of styrene-divinylbenzene copolymer. The column is eluted with methanol-water(4:1). The eluate is concentrated to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(2-methyl-1,3,4-thiadiazol-5-ylthiomethylthio)-3 -cephem-4-carboxylic acid (149 mg). Yield: 75%.

Provenance & Evidence