反应详情

Pyridinium dichromate (7.92 g, 21.0 mmol) was added to a solution of crude tert-butyl {(3R,6S)-6-(2,3-difluorophenyl)-2-[(4,4,4-trifluoro-2-hydroxybutyl)imino]azepan-3-yl}carbamate (3.27 g, 7.01 mmol) in acetonitrile (70 mL). After 70 h, the mixture was filtered and concentrated. Saturated aqueous sodium bicarbonate was added and the mixture was extracted with dichloromethane (3×). The combined organic extracts were dried over magnesium sulfate, filtered, and concentrated. Purification by silica gel chromatography (100% dichloromethane→96% dichloromethane/methanol) gave the title compound (2.35 g). MS 446.1 (M+1). 1H NMR (500 MHz, CDCl3) δ 7.14-7.09 (m, 1H), 6.97-6.94 (m, 2H), 6.33 (d, J=5.8 Hz, 1H), 4.82 (dd, J=10.0, 3.9 Hz, 1H), 4.12-4.07 (m, 1H), 3.99 (d, J=14.6 Hz, 1H), 3.37 (q, J=20.0, 10.0 Hz, 2H), 2.94 (t, J=110.2 Hz, 1H), 2.44 (d, J=13.7 Hz, 1H), 2.34-2.26 (m, 1H), 2.16-2.13 (m, 1H), 1.63-1.60 (m, 1H), 1.57 (s, 9H).

1. filtrationthe mixture was filtered
2. concentrationconcentrated
3. additionSaturated aqueous sodium bicarbonate was added
4. extractionthe mixture was extracted with dichloromethane (3×)
5. dry with materialThe combined organic extracts were dried over magnesium sulfate
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by silica gel chromatography (100% dichloromethane→96% dichloromethane/methanol)