反应详情

To a solution of 2-(3-benzyloxycarbonylamino-2-oxo-6-phenyl-1,2-dihydro-1-pyridyl)-N-(3,3,3-trifluoro-1-isopropyl-2-oxopropyl)acetamide (10 g) and anisole (6.6 g) in dichloromethane (100 mL) at 0° C. was added trifluoromethanesulphonic acid (9 mL, 15.3 g) while maintaining the temperature below 2° C. The reaction mixture was allowed to warm to room temperature in 30 min and kept at room temperature for a further 45 min before saturated aqueous sodium bicarbonate was added slowly to pH 7. Ethyl acetate was added, the phases separated and the aqueous phase extracted further with ethyl acetate. The combined organic extract was washed (brine), dried (MgSO4) and evaporated. The crude product was purified by trituration with hexane followed by trituration with diethyl ether to give the title product (which can be recrystallized from dichloromethane/hexane) as a white solid (4.85 g); TLC: Rf =0.40, ethyl acetate; 300 MHz NMR: 0.78-0.91 (m,6), 2.07-2.30 (m,1), 4.39 (d,1), 4.49 (d,1), 4.61 (t,1), 5.17 (s,1), 5.98 (d,1), 6.51 (d,1), 7.28-7.41 (m,5), 8.68 (d,1); MS: m/z=396(M+1).

1. temperaturewhile maintaining the temperature below 2° C
2. additionwas added slowly to pH 7
3. customthe phases separated
4. extractionthe aqueous phase extracted further with ethyl acetate
5. extractionThe combined organic extract
6. washwas washed (brine)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customThe crude product was purified by trituration with hexane