Lithium Hydroxide → {4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(morpholine-4-sulfonyl)benzyl]quinolin-5-yloxy}acetic Acid

HRID 2266601Notes

Reaction equation

HRID 2266601 reaction equation
C[O:2][C:3](=[O:39])[CH2:4][O:5][C:6]1[CH:15]=[CH:14][C:13]([F:16])=[C:12]2[C:7]=1[C:8]([O:35][CH:36]([F:38])[F:37])=[C:9]([CH2:19][C:20]1[CH:25]=[CH:24][C:23]([S:26]([N:29]3[CH2:34][CH2:33][O:32][CH2:31][CH2:30]3)(=[O:28])=[O:27])=[CH:22][CH:21]=1)[C:10]([CH2:17][CH3:18])=[N:11]2.[OH-].[Li+]>O1CCCC1>[F:38][CH:36]([F:37])[O:35][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:39])=[O:2])[N:11]=[C:10]([CH2:17][CH3:18])[C:9]=1[CH2:19][C:20]1[CH:21]=[CH:22][C:23]([S:26]([N:29]2[CH2:30][CH2:31][O:32][CH2:33][CH2:34]2)(=[O:27])=[O:28])=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 68781804{4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(morpholine-4-sulfonyl)benzyl]quinolin-5-yloxy}acetic Acid Methyl Ester

Product 1

HCID 16660089{4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(morpholine-4-sulfonyl)benzyl]quinolin-5-yloxy}acetic Acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {4-difluoromethoxy-2-ethyl-8-fluoro-3-[4-(morpholine-4-sulfonyl)benzyl]quinolin-5-yloxy}acetic acid methyl ester (0.16 g), tetrahydrofuran (5.0 mL) and 1.0 M aqueous lithium hydroxide solution (0.32 mL) was stirred at room temperature for 2 hour. The solvent was removed under reduced pressure and the residue was diluted with water. The pH of mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate and extracted with ethyl acetate. The combined extracts were washed with saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed under reduced pressure and the residue triturated with a mixture of acetonitrile and water to afford title compound, 0.083 g.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue was diluted with water
  3. additionThe pH of mixture was adjusted to 4 by the addition of sodium dihydrogenphosphate
  4. extractionextracted with ethyl acetate
  5. washThe combined extracts were washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was removed under reduced pressure
  8. customthe residue triturated with a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-faa1bcfcb6dc4e9ab56ac6a5937a72fe
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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