Water → HCID 67856708, compound

HRID 484431Notes

Reaction equation

HRID 484431 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([Cl:12])[CH:9]=[C:8]2[C:3]=1[C@@H:4]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[C:5](=C=O)[C@H:6](OC)[NH:7]2.[OH2:22].[OH-].[Li+].[O:25]1[CH2:29]CCC1>>[C:29]([C@H:6]1[CH2:5][C@H:4]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[C:3]2[C:8](=[CH:9][C:10]([Cl:12])=[CH:11][C:2]=2[Cl:1])[NH:7]1)([OH:25])=[O:22]

Participants

5

Reactant 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 86747045HCID 86747045, compound

Product 1

HCID 67856708HCID 67856708, compound

Procedure

To a solution of trans-5,7-dichloro-2-methoxy-carbony-4-methylsulphonylamino-1,2,3,4-tetrahydro-quinoline (0.127 g, 0.36 mmol) in tetrahydrofuran (10 ml) was added water (5 ml) and aqueous lithium hydroxide (0.80 ml of a 0.5 M solution, 0.40 mmol) and the resulting mixture was stirred at room temperature for 1.5 hours. The organic solvent was removed in vacuo and to the aqueous residue was added dilute sodium hydrogen carbonate solution (40 ml). The mixture was washed with ethyl acetate (30 ml), the pH of the aqueous layer was adjusted to 1 with dilute hydrochloric acid and extracted with ethyl acetate (2×40 ml). The combined organic extracts were washed with brine (40 ml), dried (Na2SO4) and evaporated to give the crude product which was triturated with diethyl ether to give the title compound as colourless crystals (0.08 g, m.p. 194°-195° C.); δ (360 MHz, DMSO) 1.60 (1H, m, CHACHBHCCHD), 2.47 (1H, m, CHACHBHCCHD), 3.04 (3H, s, CH3), 4.00 (1H, m, CHACHBHCCHD), 4.65 (1H, m, CHACHBHCCHD), 6.64 (1H, d, J=1.9 Hz, 6-H or 8-H), 6.76 (1H, br, s, ArNH), 6.84 (1H, d, J=1.9 Hz, 6-H or 8-H), 7.43 (1H, d, J=5.8 Hz, CHNHSO2CH3); m/e (FAB) 337 (M-1); Found: C, 39.13; H, 3.60; N, 8.02; C11H12Cl2N2O4S requires C, 38.95; H, 3.57; N, 8.26%.

Workup

  1. customThe organic solvent was removed in vacuo and to the aqueous residue
  2. additionwas added dilute sodium hydrogen carbonate solution (40 ml)
  3. washThe mixture was washed with ethyl acetate (30 ml)
  4. extractionextracted with ethyl acetate (2×40 ml)
  5. washThe combined organic extracts were washed with brine (40 ml)
  6. dry with materialdried (Na2SO4)
  7. customevaporated
  8. customto give the crude product which
  9. customwas triturated with diethyl ether

Sources & evidence

ORD record
ord-632cb2eede7c41fbaa1dba9d6531b728
Source dataset
uspto-grants-1993_07
Patent number
US05231102

Reaction notes

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