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 7 hours. At the end of this time, the reaction mixture was allowed to stand overnight at room temperature. The solvent was then removed from the reaction mixture by distillation under reduced pressure. Water was added to the resulting 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. 2 ml of anhydrous tetrahydrofuran were added to the residue, and then 0.33 ml of triethylamine and 0.23 ml of ethyl chloroformate were added dropwise, whilst ice-cooling. The resulting mixture was stirred at room temperature for 2 hours. The solvent was then 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, and the residue was subjected to silica gel column chromatography, using 1:3 and 1:2 by volume mixtures of ethyl acetate and hexane as eluent, followed by reverse phase preparative silica gel column chromatography, using a 1:1 by volume mixture 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 75 mg of the title compound as a red oil having an Rf value of 0.46 (silica gel thin layer chromatography; using a 1:2 by volume mixture of ethyl acetate and hexane as the developing solvent).

1. waitto stand overnight at room temperature
2. customThe solvent was then removed from the reaction mixture by distillation under reduced pressure
3. additionWater was added to the resulting 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. addition2 ml of anhydrous tetrahydrofuran were added to the residue
10. addition0.33 ml of triethylamine and 0.23 ml of ethyl chloroformate were added dropwise, whilst ice-
11. temperaturecooling
12. stirringThe resulting mixture was stirred at room temperature for 2 hours
13. customThe solvent was then removed from the reaction mixture by distillation under reduced pressure
14. additionWater was added to the residue
15. extractionafter which it was extracted with ethyl acetate
16. washThe extract was washed with a saturated aqueous solution of sodium chloride
17. dry with materialdried over anhydrous sodium sulfate
18. customEthyl acetate was removed from the
19. extractionextract by distillation under reduced pressure
20. additionby volume mixture of acetonitrile and water as eluent
21. customAcetonitrile was removed from the eluate
22. customso obtained by distillation under reduced pressure
23. extractionthe residue was extracted with ethyl acetate
24. washThe extract was washed with a saturated aqueous solution of sodium chloride
25. dry with materialdried over anhydrous sodium sulfate
26. customEthyl acetate was removed from the
27. extractionextract by distillation under reduced pressure
28. dissolutionThe residue was dissolved in dioxane