反应详情

25 ml of methanol and 25 ml of tetrahydrofuran were added to 6.2 g (18 mmol) of methyl (2R)-t-butoxycarbonylamino-3-(4-iodophenyl)propionate. 3.44 g (91 mmol) of sodium borohydride was added to the resultant mixture under cooling with ice, and they were stirred for 17 hours. The reaction liquid was slowly poured into 1 N hydrochloric acid. After the extraction with ethyl acetate, the organic layer was successively washed with water, 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated. 50 ml of dichloromethane was added to the residue. Then, 5.02 ml (36 mmol) of triethylamine and 3.09 g (27 mmol) of methanesulfonyl chloride were added to the resultant mixture under cooling with ice, and they were stirred for 30 minutes. The temperature was elevated to room temperature, and the mixture was stirred for 15 hours. The reaction liquid was diluted with water. After the extraction with dichloromethane, the organic layer was successively washed with 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. 40 ml of dimethylformamide and 3.85 g (91 mmol) of lithium chloride were added to the residue, and they were stirred at 50° C. for 19 hours. The reaction liquid was diluted with water. After the extraction with ethyl acetate, the organic layer was successively washed with water and saturated aqueous NaCl solution. The solvent was evaporated, and the residue was purified by the silica gel column chromatography to obtain the title compound.

1. temperatureunder cooling with ice, and they
2. customThe reaction liquid
3. extractionAfter the extraction with ethyl acetate
4. washthe organic layer was successively washed with water, 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated
7. addition50 ml of dichloromethane was added to the residue
8. temperatureunder cooling with ice, and they
9. stirringwere stirred for 30 minutes
10. customwas elevated to room temperature
11. stirringthe mixture was stirred for 15 hours
12. customThe reaction liquid
13. extractionAfter the extraction with dichloromethane
14. washthe organic layer was successively washed with 1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution
15. dry with materialdried over anhydrous magnesium sulfate
16. customThe solvent was evaporated under reduced pressure
17. stirringwere stirred at 50° C. for 19 hours
18. customThe reaction liquid
19. extractionAfter the extraction with ethyl acetate
20. washthe organic layer was successively washed with water and saturated aqueous NaCl solution
21. customThe solvent was evaporated
22. customthe residue was purified by the silica gel column chromatography