Nitromethane → HCID 178481917, compound

Participants

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(2-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid diphenylmethyl ester (1.39 g: 1.34 mMol.) in a mixture anisole (5 ml) and nitromethane (20 ml) is added dropwise a solution of aluminum chloride (1.43 g: 10.8 mMol.) in anisole (5 ml) at -40° C. After stirring at -30° to -40° C. for 1 hour, the mixture is diluted with 1N-hydrochloric acid (11 ml) and water and washed with ethyl acetate. The aqueous layer is concentrated under reduced pressure to remove organic solvents and passed through a column of styrene-divinylbenzene copolymer adsorbent. The product is eluted with methanol-water (4:1) to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-(2-methyl-1,2,3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid as pale yellow powder (534 mg). Yield: 75%.

Provenance & Evidence