Water → HCID 25003109, compound

HRID 215828Notes

Reaction equation

HRID 215828 reaction equation
C[O:2][C:3](=[O:35])[C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:12]=[N:13][C:14]([O:17][CH2:18][C:19]3[C:20]([C:27]4[C:32]([Cl:33])=[CH:31][CH:30]=[CH:29][C:28]=4[Cl:34])=[N:21][O:22][C:23]=3[CH:24]([CH3:26])[CH3:25])=[CH:15][CH:16]=2)=[CH:6][CH:5]=1.[OH-].[Na+].O>CO>[Cl:33][C:32]1[CH:31]=[CH:30][CH:29]=[C:28]([Cl:34])[C:27]=1[C:20]1[C:19]([CH2:18][O:17][C:14]2[N:13]=[CH:12][C:11]([O:10][C:7]3[CH:6]=[CH:5][C:4]([C:3]([OH:35])=[O:2])=[CH:9][CH:8]=3)=[CH:16][CH:15]=2)=[C:23]([CH:24]([CH3:26])[CH3:25])[O:22][N:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 44248243HCID 44248243, compound

Product 1

HCID 25003109HCID 25003109, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-{6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid methyl ester (0.070 g, 0.14 mmol) in methanol (5 ml) was added NaOH (0.104 g, 2.6 mmol) and water (0.25 ml) and the reaction mixture was stirred at room temperature for 30 h. Then solvent was evaporated, water (1.5 ml) was added and the mixture was acidified to pH 6 with 1N hydrochloric acid and the resulting solution was extracted with ethyl acetate. The extract was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure to afford 4-{6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid as colorless oil. Yield: 0.037 g (53%).

Workup

  1. customThen solvent was evaporated
  2. additionwater (1.5 ml) was added
  3. extractionthe resulting solution was extracted with ethyl acetate
  4. dry with materialThe extract was dried over anhydrous Na2SO4
  5. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d0a4b36a33ad4f0e8adf386240d4bcc2
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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