Aluminum(III) Chloride → (6R,7R)-7-[[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-hydroxyiminoacetyl]amino]-8-oxo-3-(pyridin-2-ylsulfanylmethylsulfanyl)-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid

Participants

Reaction Conditions

Reaction Steps

To a solution of 7β-[(Z)-2-(2-t-butoxycarbonylaminothiazol-4-yl)-2-trityloxyiminoacetamido]-3-(2-pyridylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (722 mg: 0.70 mMol.) in a mixture of anisole (2 ml) and nitromethane (8 ml) cooling at -40° C. is added a solution of aluminum chloride (744 mg; 5.59 mMol. ) in anisole (2 ml), and the mixture is stirred at -30° to -40° C. for 1 hour. The reaction mixture is diluted with 1N-hydrochloric acid (6 ml) and water, washed with ethyl acetate, concentrated under reduced pressure to remove the organic solvents, and passed through a styrene-divinylbenzene copolymer column. The adsorbed material is eluted with methanol-water (4:1). The eluate is concentrated. The residue is washed with ethyl acetate and dried to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetylamino]-3-(2-pyridylthiomethylthio)-3-cephem-4-carboxylic acid (289 mg). Yield: 79%.

Provenance & Evidence