反应详情

To a solution containing 906 mg of sodium 3-hydroxymethyl-7β-[2-(2-tritylaminothiazol-4-yl)-(Z)-2-trityloxyiminoacetamido]-3-cephem-4-carboxylate and 309 mg of 2-amidinomethylthio -5-mercapto-1,3,4-thiadiazole in 7 ml of DMF was added 1.01 g of ethyl o-phenylenephosphate under ice-cooling and stirring. The reaction mixture was stirred at room temperature for 4 hours and subjected to a column chromatography on silica gel (100 g), being washed with acetone and eluted with acetone/water (9:1). The eluate was concentrated to dryness under reduced pressure, and there was added 20 ml of formic acid. The mixture was stirred at room temperature for 16 hours and then distilled to remove formic acid. To the residue was added a mixture of water and THF. The solution was washed with ethyl acetate, concentrated under reduced pressure and then subjected to a column chromatography on XAD-II (140 ml), being washed with water and eluted with 20% aqueous ethanol. The eluate was concentrated to 10 ml and the resultant precipitate was collected by filtration to give 160 mg of the title compound as pale yellow crystals.

1. temperaturecooling
2. stirringThe reaction mixture was stirred at room temperature for 4 hours
3. washbeing washed with acetone
4. washeluted with acetone/water (9:1)
5. concentrationThe eluate was concentrated to dryness under reduced pressure, and there
6. additionwas added 20 ml of formic acid
7. stirringThe mixture was stirred at room temperature for 16 hours
8. distillationdistilled
9. customto remove formic acid
10. additionTo the residue was added
11. additiona mixture of water and THF
12. washThe solution was washed with ethyl acetate
13. concentrationconcentrated under reduced pressure
14. washbeing washed with water
15. washeluted with 20% aqueous ethanol
16. concentrationThe eluate was concentrated to 10 ml
17. filtrationthe resultant precipitate was collected by filtration