Lithium Hydroxide → HCID 67856807, compound

Participants

Reaction Steps

To a solution of trans-5,7-dichloro-2-methoxycarbonyl-4-phenyl(methoxy)methylcarbonylamino-1,2,3,4-tetrahydroquinoline (Isomer B) (0.140 g, 0.331 mmol) (Example 44a) in a mixture of tetrahydrofuran (10 ml) and water (5 ml) was added aqueous lithium hydroxide (0.73 ml of a 0.5M solution, 0.364 mmol) and the resulting mixture was stirred at room temperature for 2 h. The organic solvent was removed under vacuum and the residue was diluted with sodium bicarbonate solution (50 ml) then 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 bring (1×40 ml), dried (MgSO4) and evaporated to give the crude product which was recrystallised from hot ethyl acetate/petroleum ether (bp 60°-80° ) to give the title compound as colourless crystals (0.070 g), m.p. 238°-239° C. δ (360 MHz, DMSO) 1.63 (1H, ddd, J=13.2, 12.6 and 4.0 Hz, CHACHBHCCHD), 2.07 (1H, dm, J=13.2 Hz, CHACHBHCCHD), 3.28 (3H, s, NHCOCH(OCH3)Ph), 3.83 (1H, dd, J=12.6 and 2.6 Hz, CHACHBHCCHD), 4.67 (1H, s, NHCOCH(OCH3)Ph), 5.04 (1H, m, CHACHBHCCHDNHCO), 6.66 (1H, d, J=2.0 Hz, 6-H or 8-H), 6.77 (1H, s, ArNH), 6.88 (1H, d, J=2.0 Hz, 6-H or 8-H), 7.26-7.40 (5H, m, ArH), 8.49 (1H, d, J=7.4 Hz, CHDNHCO); m/e(CI+) 409 (M+H), 166 (100%); Found C, 55.77; H, 4.57; N, 6.64; C19H18Cl2N2O4 requires C, 55.76; H, 4.43; N, 6.85%.

Provenance & Evidence