Hydrochloric Acid → 3-(3-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-fluorophenyl)propanoic acid

HRID 709684Notes

Reaction equation

HRID 709684 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:19][CH2:20][C:21]([O:23]C)=[O:22])[CH:15]=[C:16]([F:18])[CH:17]=2)[CH:7]=[CH:6][C:5]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33].[OH-].[Na+].Cl>CO.C1COCC1.O>[CH3:1][C:2]([CH3:35])([CH3:34])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:19][CH2:20][C:21]([OH:23])=[O:22])[CH:15]=[C:16]([F:18])[CH:17]=2)[CH:7]=[CH:6][C:5]=1[C:25]1[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=1[F:33]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117759844Methyl 3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-fluorophenyl)propanoate

Product 1

HCID 1177601013-(3-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-fluorophenyl)propanoic acidYield 78.6%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-fluorophenyl)propanoate (380 mg) in methanol (4.0 mL) and THF (3.0 mL) was added a solution of sodium hydroxide (183 mg) in water (4.0 mL), and the mixture was stirred at room temperature for 15 hr. 2N Hydrochloric acid was added to the reaction to mixture to adjust to pH<2, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (290 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-08e9652784f5493eae7f0f8575b9be3a
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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