反应详情

0.56 ml (7.73 mmol) of thionyl chloride was added to 3 ml of methanol under cooling with ice. 450 mg (1.56 mmol) of L-4-iodophenylalanine was added to the resultant mixture, and they were heated under reflux for 2 hours. The solvent was evaporated. 0.52 ml (4.68 mmol) of N-methylmorpholine, 443 mg (2.03 mmol) of di-t-butyl carbonate and 10 ml of dichloromethane were added to the residue, and they were stirred for 19 hours. The reaction liquid was diluted with water. After the extraction with dichloromethane, the organic layer was washed with saturated aqueous sodium hydrogencarbonate solution and then with saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. 3 ml of methanol and 3 ml of tetrahydrofuran were added to the residue. 143 mg (3.78 mmol) of sodium borohydride was added to the resultant mixture, 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 dried over anhydrous magnesium sulfate. The solvent was evaporated. The residue was purified by the silica gel column chromatography to obtain the title compound.

1. temperatureunder cooling with ice
2. temperaturewere heated
3. temperatureunder reflux for 2 hours
4. customThe solvent was evaporated
5. customThe reaction liquid
6. extractionAfter the extraction with dichloromethane
7. washthe organic layer was washed with saturated aqueous sodium hydrogencarbonate solution
8. dry with materialwith saturated aqueous NaCl solution, and then dried over anhydrous magnesium sulfate
9. customThe solvent was evaporated under reduced pressure
10. addition3 ml of methanol and 3 ml of tetrahydrofuran were added to the residue
11. stirringwere stirred for 17 hours
12. customThe reaction liquid
13. extractionAfter the extraction with ethyl acetate
14. washthe organic layer was successively washed with water
15. dry with material1 N hydrochloric acid, 1 N sodium hydroxide and saturated aqueous NaCl solution, and dried over anhydrous magnesium sulfate
16. customThe solvent was evaporated
17. customThe residue was purified by the silica gel column chromatography