反应详情

0.18 ml of triethylamine and 0.07 ml of methanesulfonyl chloride were added in order to a chloroform (5 ml) solution of 100 mg of N-(4-(1,4-dihydroxy-2-methylbutyl)-3-fluorophenyl)pyridine-2-carboxamide, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 23 mg of sodium azide was added to a dimethylformamide (4 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled to room temperature, water was added to it, extracted with ethyl acetate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate were added in order to a methanol (5 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 15 minutes. The reaction liquid was cooled to room temperature, and then aqueous saturated sodium bicarbonate was added to it, extracted with chloroform and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 0.08 ml of triethylamine, 0.07 ml of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine were added in order to a chloroform (4 ml) solution of the resulting residue, and the reaction liquid was stirred at room temperature for 30 minutes. Aqueous saturated sodium bicarbonate was added to the reaction liquid, extracted with chloroform, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1) to obtain the entitled compound as a colorless oily substance.

1. customthe reaction liquid
2. extractionextracted with chloroform
3. dry with materialdried with anhydrous sodium sulfate
4. customThe solvent was evaporated away under reduced pressure, and 23 mg of sodium azide
5. additionwas added to a dimethylformamide (4 ml) solution of the resulting residue
6. customthe reaction liquid
7. stirringwas stirred at 40° C. for 2 hours
8. customThe reaction liquid
9. temperaturewas cooled to room temperature
10. extractionextracted with ethyl acetate
11. dry with materialdried with anhydrous sodium sulfate
12. customThe solvent was evaporated away under reduced pressure, and 50 mg of sodium borohydride and 5 mg of copper sulfate pentahydrate
13. additionwere added in order to a methanol (5 ml) solution of the resulting residue
14. customthe reaction liquid
15. stirringwas stirred at 40° C. for 15 minutes
16. customThe reaction liquid
17. temperaturewas cooled to room temperature
18. extractionextracted with chloroform
19. dry with materialdried with anhydrous sodium sulfate
20. customThe solvent was evaporated away under reduced pressure, and 0.08 ml of triethylamine, 0.07 ml of acetic anhydride and 5 mg of N,N-4-dimethylaminopyridine
21. additionwere added in order to a chloroform (4 ml) solution of the resulting residue
22. customthe reaction liquid
23. stirringwas stirred at room temperature for 30 minutes
24. extractionextracted with chloroform
25. dry with materialdried with anhydrous sodium sulfate
26. customThe solvent was evaporated away under reduced pressure
27. customthe resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=100/1)
28. customto obtain the entitled compound as a colorless oily substance