反应详情

2 ml of methanol and 2 ml of butylamine were added to a solution of 1.6 mmol of 2-[5(1,2-dithiolan-3-yl)pentyl]isoindole-1,3-dione in 3 ml of toluene. The resulting mixture was stirred at room temperature for 6 hours. The reaction mixture was then allowed to stand overnight at room temperature. At the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue, after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. 5 ml of pyridine were then added to the residue. 0.31 ml of propionic anhydride was added dropwise to the resulting mixture, and then the mixture was stirred at room temperature for 2 hours and 30 minutes. The solvent was removed from the reaction mixture by distillation under reduced pressure. Water was added to the residue after which it was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. The residue was thereafter subjected to silica gel column chromatography, using 2:1, 3:1 and 1:0 by volume mixtures of ethyl acetate and hexane as eluent, followed by reverse phase preparative silica gel column chromatography, using 1:4, 3:7, 2:3 and 1:1 by volume mixtures of acetonitrile and water as eluent. Acetonitrile was removed from the eluate so obtained by distillation under reduced pressure, and the residue was extracted with ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride and then dried over anhydrous sodium sulfate. Ethyl acetate was removed from the extract by distillation under reduced pressure. The residue was dissolved in dioxane, after which it was lyophilised, to give 125 mg of the title compound as a yellow oil having an Rf value of 0.45 (silica gel thin layer chromatography; using ethyl acetate as the developing solvent).

1. waitto stand overnight at room temperature
2. customAt the end of this time, the solvent was removed from the reaction mixture by distillation under reduced pressure
3. additionWater was added to the residue
4. extractionafter which it was extracted with ethyl acetate
5. washThe extract was washed with a saturated aqueous solution of sodium chloride
6. dry with materialdried over anhydrous sodium sulfate
7. customEthyl acetate was removed from the
8. extractionextract by distillation under reduced pressure
9. addition5 ml of pyridine were then added to the residue
10. addition0.31 ml of propionic anhydride was added dropwise to the resulting mixture
11. stirringthe mixture was stirred at room temperature for 2 hours and 30 minutes
12. customThe solvent was removed from the reaction mixture by distillation under reduced pressure
13. additionWater was added to the residue after which it
14. extractionwas extracted with ethyl acetate
15. washThe extract was washed with a saturated aqueous solution of sodium chloride
16. dry with materialdried over anhydrous sodium sulfate
17. customEthyl acetate was removed from the
18. extractionextract by distillation under reduced pressure
19. customAcetonitrile was removed from the eluate
20. customso obtained by distillation under reduced pressure
21. extractionthe residue was extracted with ethyl acetate
22. washThe extract was washed with a saturated aqueous solution of sodium chloride
23. dry with materialdried over anhydrous sodium sulfate
24. customEthyl acetate was removed from the
25. extractionextract by distillation under reduced pressure
26. dissolutionThe residue was dissolved in dioxane