Hydrochloric Acid → 3-Cyclopropyl-3-(3-((5-(2,2-dimethylpropyl)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methoxy)phenyl)propanoic acid

HRID 709783Notes

Reaction equation

HRID 709783 reaction equation
[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([C:29]4[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=4[F:37])=[C:22]([CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH:23]=3)[CH:11]=2)[CH2:5][C:6]([O:8]C)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1.CO>[CH:1]1([CH:4]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([O:16][CH2:17][C:18]3[CH:19]=[N:20][C:21]([C:29]4[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=4[F:37])=[C:22]([CH2:24][C:25]([CH3:28])([CH3:26])[CH3:27])[CH:23]=3)[CH:11]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117760067Methyl 3-cyclopropyl-3-(3-((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methoxy)phenyl)propanoate

Product 1

HCID 716647453-Cyclopropyl-3-(3-((5-(2,2-dimethylpropyl)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)methoxy)phenyl)propanoic acidYield 92.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 3-cyclopropyl-3-(3-((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)methoxy)phenyl)propanoate (143 mg) in THF (2.0 mL) and methanol (1.0 mL) was added 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was stirred at room temperature for 4 hr. 1N Hydrochloric acid (2.0 mL) was added to the reaction mixture at room temperature, and the mixture was extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. After silica gel filtration, the solvent was evaporated under reduced pressure to give the title compound (129 mg) as a white amorphous solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationAfter silica gel filtration
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-ceb9dd2eaa854282a1002c7a5843eb16
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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