反应详情

To a solution of trans-5,7-dichloro-2-methoxycarbonyl-4-phenyl(methoxy)methylcarbonylamino-1,2,3,4-tetrahydroquinoline (Isomer A, 0.180 g, 0.426 mmol) in a mixture of tetrahydrofuran (10 ml) and water (5 ml) was added aqueous lithium hydroxide (0.904 ml of a 0.50M solution, 0.47 mmol), and the resulting mixture was stirred at room temperature for 3 h. The solvent was then removed under vacuum and the residue was diluted with sodium bicarbonate solution (50 ml) and washed with diethyl ether (1×30 ml). The aqueous layer was separated, acidified with concentrated hydrochloric acid and extracted with ethyl acetate (2×40 ml). The combined extracts were washed with saturated brine (1×40 ml), dried (MgSO4) and evaporated to give a solid which was recrystallised from hot ethyl acetate/petroleum ether (bp 60°-80°) to give the title compound as colourless crystals (0.102 g), m.p. 232°-233° C. δ (360 MHz, DMSO) 1.63 (1H, ddd, J=13.2, 12.6 and 4.1 Hz, CHACHBHCCHD), 2.11 (1H, dd, J=13.2 Hz, CHACHBHCCHD), 3.27 (3H, s, NHCOCH(OCH3)Ph), 3.90 (1H, dd, J=12.6 and 7.7 Hz, CHACHBHCCHD), 4.64 (1H, s, NHCOCH(OCH3)Ph), 5.00 (1H, m, CHACHBHCCHDNHCO), 6.63 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.78 (1H, s, ArNH), 6.88 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.27-7.41 (5H, m, ArH), 8.48 (1H, d, J=7.4 Hz, CHDNHCO); m/e (CI+) 409 (M+H), 166 (100%); Found C, 55.83; H, 4.46; N, 6.81; C19H18Cl2N2O4 requires C, 55.76; H, 4.43 ; N, 6.85%.

1. customThe solvent was then removed under vacuum
2. additionthe residue was diluted with sodium bicarbonate solution (50 ml)
3. washwashed with diethyl ether (1×30 ml)
4. customThe aqueous layer was separated
5. extractionextracted with ethyl acetate (2×40 ml)
6. washThe combined extracts were washed with saturated brine (1×40 ml)
7. dry with materialdried (MgSO4)
8. customevaporated
9. customto give a solid which
10. customwas recrystallised from hot ethyl acetate/petroleum ether (bp 60°-80°)