Lithium Hydroxide → HCID 86755991, compound

HRID 370048Notes

Reaction equation

HRID 370048 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) δ 6.39 (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-c878f568dcfe45eeb67462848477984e
Source dataset
uspto-grants-2000_10
Patent number
US06140342

Reaction notes

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