Lithium Hydroxide → [4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-yl-benzyl)quinolin-5-yloxy]acetic acid

HRID 1944276Notes

Reaction equation

HRID 1944276 reaction equation
C[O:2][C:3](=[O:35])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:31][CH:32]([F:34])[F:33])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]3[CH:30]=[CH:29][CH:28]=[N:27]3)=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[F:34][CH:32]([F:33])[O:31][C:8]1[C:7]2[C:12](=[C:13]([F:16])[CH:14]=[CH:15][C:6]=2[O:5][CH2:4][C:3]([OH:35])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]2[CH:30]=[CH:29][CH:28]=[N:27]2)=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 67458307[4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester

Product 1

HCID 24995212[4-Difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-yl-benzyl)quinolin-5-yloxy]acetic acidYield 97.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of [4-difluoromethoxy-2-ethyl-8-fluoro-3-(4-pyrazol-1-ylbenzyl)quinolin-5-yloxy]acetic acid methyl ester (0.19 g) in tetrahydrofuran (5.0 mL) was treated with 1.0 M aqueous lithium hydroxide solution (0.78 ml), and the resulting solution was stirred at room temperature for 1 hour. The tetrahydrofuran was removed under reduced pressure and the residue acidified by the addition of 0.1M aqueous hydrochloric acid. The mixture was extracted with ethyl acetate and the combined extracts were washed with saturated aqueous sodium chloride solution, and than dried over magnesium sulfate. The solvent was removed under reduced pressure to afford title compound (0.18 g).

Workup

  1. customThe tetrahydrofuran was removed under reduced pressure
  2. additionthe residue acidified by the addition of 0.1M aqueous hydrochloric acid
  3. extractionThe mixture was extracted with ethyl acetate
  4. washthe combined extracts were washed with saturated aqueous sodium chloride solution
  5. dry with materialthan dried over magnesium sulfate
  6. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-a1c2bb6131e24d8aa4710f62a9bf4d1f
Source dataset
uspto-grants-2013_03
Patent number
US08394830B2

Reaction notes

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