Lithium Hydroxide → HCID 67856807, compound

HRID 484438Notes

Reaction equation

HRID 484438 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:5][C@H:6]([C:19]([O:21]C)=[O:20])[N:7]2[NH:13][C:14]([CH2:16][O:17][CH3:18])=[O:15].[OH-].[Li+]>O1CCCC1.O>[C:19]([C@H:6]1[CH2:5][C@H:4]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[N:7]1[NH:13][C:14]([CH2:16][O:17][CH3:18])=[O:15])([OH:21])=[O:20]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 67690853HCID 67690853, compound

Product 1

HCID 67856807HCID 67856807, compoundYield 58.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

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%.

Workup

  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°)

Sources & evidence

ORD record
ord-e4d0eecbd3074723a43d7aca8eb58bbb
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

Loading…