Lithium Hydroxide → HCID 86755991, compound

HRID 279376Notes

Reaction equation

HRID 279376 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH:14]=2)[C@H:9]([N:29]([CH2:34][C:35]2[CH:40]=[C:39]([C:41]([F:44])([F:43])[F:42])[CH:38]=[C:37]([C:45]([F:48])([F:47])[F:46])[CH:36]=2)[C:30]([O:32][CH3:33])=[O:31])[CH2:8][C@@H:7]1[CH3:49])=[O:5])[CH3:2].[OH-].[Li+]>C1COCC1.CO>[CH2:1]([O:3][C:4]([N:6]1[C:15]2[C:10](=[CH:11][C:12]([O:27][CH3:28])=[C:13]([O:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:14]=2)[C@H:9]([N:29]([CH2:34][C:35]2[CH:36]=[C:37]([C:45]([F:47])([F:48])[F:46])[CH:38]=[C:39]([C:41]([F:44])([F:42])[F:43])[CH:40]=2)[C:30]([O:32][CH3:33])=[O:31])[CH2:8][C@@H:7]1[CH3:49])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 86755992HCID 86755992, compound

Product 1

HCID 86755991HCID 86755991, compoundYield 92.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Prepared by treating a solution of cis-4-[(3,5-bis-trifluoromethyl-benzyl)-methoxycarbonyl-amino]-7-(5-ethoxycarbonyl-pentyloxy)-6-methoxy-2-methyl-3,4-dihydro-2H-quinoline-1-carboxylic acid ethyl ester (Example 163) (27 mg, 0.04 mmol) in 0.6 mL THF and 0.2 mL methanol with an aqueous 1M lithium hydroxide solution (0.2 mL, 0.2 mmol) at room temperature. After 45 minutes, acidification with 1N HCl and extraction with ethyl acetate, drying the organic extracts over sodium sulfate, and concentration under reduced pressure provided 25 mg of the title compound. MS m/z 697 (M++19), 378 (M+−300); 1H NMR (CDCl3) δ6.39 (C5, s, 1H), 3.79 (C6-OMe, s, 3H), 1.16 (Me, d, 3H, J=6.1 Hz).

Workup

  1. customPrepared
  2. extractionacidification with 1N HCl and extraction with ethyl acetate
  3. customdrying the organic extracts
  4. concentrationover sodium sulfate, and concentration under reduced pressure

Sources & evidence

ORD record
ord-7c553d7a676244c9b7959e7b2b8b59b0
Source dataset
uspto-grants-2002_03
Patent number
US06362198B1

Reaction notes

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