Sodium Hydroxide → 3-{6-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid

HRID 215832Notes

Reaction equation

HRID 215832 reaction equation
[OH-].[Na+].C([O:5][C:6](=[O:38])[C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([O:13][C:14]2[CH:15]=[N:16][C:17]([O:20][CH2:21][C:22]3[C:23]([C:30]4[C:35]([Cl:36])=[CH:34][CH:33]=[CH:32][C:31]=4[Cl:37])=[N:24][O:25][C:26]=3[CH:27]([CH3:29])[CH3:28])=[CH:18][CH:19]=2)[CH:8]=1)C>O.C(O)C>[Cl:36][C:35]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:37])[C:30]=1[C:23]1[C:22]([CH2:21][O:20][C:17]2[N:16]=[CH:15][C:14]([O:13][C:9]3[CH:8]=[C:7]([CH:12]=[CH:11][CH:10]=3)[C:6]([OH:38])=[O:5])=[CH:19][CH:18]=2)=[C:26]([CH:27]([CH3:29])[CH3:28])[O:25][N:24]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 672972823-{6-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid ethyl ester

Product 1

HCID 250031103-{6-[3-(2,6-Dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

NaOH (0.228 g, 5.7 mmol) in water (0.25 ml) was added to a solution of 3-{6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid ethyl ester (0.157 g, 0.3 mmol) in ethanol (5 ml) and the reaction mixture was stirred at room temperature for 50 h. The solvent was removed under reduced pressure and the residue diluted with water (1.5 ml) and acidified to pH 6. The resulting solution was extracted with ethyl acetate and the extract was dried over anhydrous Na2SO4. The solvent was removed under reduced pressure to afford 3-{6-[3-(2,6-dichloro-phenyl)-5-isopropyl-isoxazol-4-ylmethoxy]-pyridin-3-yloxy}-benzoic acid as colorless oil. Yield 0.14 g (33%).

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionthe residue diluted with water (1.5 ml)
  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-c7b273c3f23a430cbcbf7a4a1f28ee25
Source dataset
uspto-grants-2012_06
Patent number
US08193192B2

Reaction notes

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