反应详情

155 mg of triethylamine and 130 mg of methanesulfonyl chloride were added in order to a chloroform (8 ml) solution of 165 mg of N-(4-(2-((t-butyl(dimethyl)silyl)oxy)-1,4-dihydroxybutyl)-3-fluorophenyl)pyridine-2-carboxamide, with cooling with ice, and the reaction liquid was stirred at room temperature for 30 minutes. The reaction liquid was diluted with chloroform, washed with aqueous saturated sodium bicarbonate, and dried with anhydrous sodium sulfate. The solvent was evaporated away under reduced pressure, and 25 mg of sodium azide was added to a dimethylformamide (5 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled, 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 (10 ml) solution of the resulting residue, and the reaction liquid was stirred at 40° C. for 2 hours. The reaction liquid was cooled, 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 the resulting residue was purified through silica gel column chromatography (developing solvent: chloroform/methanol=50/1) to obtain the entitled compound as a colorless oily substance.

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