反应详情

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%.

1. concentrationThe reaction mixture is concentrated
2. washThe residue is washed with ether
3. filtrationfiltered
4. customend dried
5. additionTo a solution of this residue in a mixture of anisole (2 ml) and nitro- methane (8 ml) at -40° C.
6. stirringthe mixture is stirred at -30° to -40° C. for 1 hour
7. washwashed with ethyl acetate
8. concentrationconcentrated under reduced pressure
9. customto remove organic solvents
10. washThe residue is washed with ethyl acetate
11. customresulting powder
12. custompurified by chromatography over analytical styrene-divinylbenzene (water)