Sodium Bicarbonate → HCID 178508511, compound

Participants

Reaction Steps

A solution of 7β-[(Z)-2-(2-tritylaminothiazol-4-yl)-2-(diphenylmethoxycarbonylmethoxyimino)acetamido]-3-(trityl-1,2,3-triazol-4-ylthio-methylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (1.04 g: 0.749 mMol.) in a mixture of 98% formic acid (16 ml) and water (0.8 ml) is stirred at room temperature for 3 hours. The reaction mixture is concentrated. The residue is washed with ether, filtered, end dried. To a solution of this residue in a mixture of anisole (2 ml) and nitro- methane (8 ml) at -40° C. is added a solution of aluminum chloride (0.50 g: 3.76 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 (3.8 ml) and water, washed with ethyl acetate, and concentrated under reduced pressure to remove organic solvents. The remaining aqueous solution is subjected to chromatography over styrene-divinyl-benzene copolymer (methanol: water=4:1). The residue is washed with ethyl acetate and resulting powder is dissolved in dilute aqueous sodium hydrogen carbonate, and purified by chromatography over analytical styrene-divinylbenzene (water). The eluate is lyophilized and pulverized with ethyl acetate to give 7β-[(Z)-2-(2-aminothiazol-4-yl)-2-(sodiooxycarbonylmethoxyimino)acetamido]-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid sodium salt (121 mg) as pale yellow white powder. Yield: 26%.

Provenance & Evidence