反应详情

5 ml of anhydrous tetrahydrofuran were added to 6 ml of a mixture of 2.5 mmol of 3-(1,2-dithiolan-3-yl)propionic acid in a mixture of ethyl acetate and dimethylformamide. 0.6 ml of triethylamine, 349 mg of β-alanine methyl ester hydrochloride and 0.38 ml of diethyl cyanophosphate were added to the reaction solution, whilst ice-cooling, and the resulting mixture was stirred, whilst ice-cooling for 1 hour. At the end of this time, the reaction mixture was stirred at room temperature for 30 minutes, and then the solvent was removed from the reaction mixture by evaporation under reduced pressure. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was subjected to silica gel column chromatography, using 2:1, 3:1 and 1:0 by volume mixtures of ethyl acetate and hexane as the eluent. The residue was then subjected to reverse phase preparative silica gel column chromatography, using a 2:3 by volume mixture of acetonitrile and water as eluent, and the acetonitrile was removed from the solution by evaporation under reduced pressure, after which the residue was extracted with ethyl acetate. The extraction solution was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous sodium sulfate. The ethyl acetate was removed from the extraction solution by evaporation under reduced pressure, and the residue was dissolved in dioxane and then lyophilised, to obtain 22.9 mg of the title compound as a yellow oil having an Rf value of 0.24 (silica gel thin layer chromatography; using a 3:1 by volume mixture of ethyl acetate and hexane as developing solvent).

1. temperaturecooling
2. temperaturecooling for 1 hour
3. stirringAt the end of this time, the reaction mixture was stirred at room temperature for 30 minutes
4. customthe solvent was removed from the reaction mixture by evaporation under reduced pressure
5. additionWater was added to the residue
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
8. dry with materialdried over anhydrous sodium sulfate
9. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
10. additionby volume mixture of acetonitrile and water as eluent
11. customthe acetonitrile was removed from the solution by evaporation under reduced pressure
12. extractionafter which the residue was extracted with ethyl acetate
13. washThe extraction solution was washed with a saturated aqueous solution of sodium chloride
14. dry with materialdried over anhydrous sodium sulfate
15. customThe ethyl acetate was removed from the extraction solution by evaporation under reduced pressure
16. dissolutionthe residue was dissolved in dioxane