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

HRID 1049471Notes

Reaction equation

[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([C:30]4[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=4[F:38])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C1COCC1.CO>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([C:30]4[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=4[F:38])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-(((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)oxy)methyl)phenyl)propanoate (253 mg) in THF (4.0 mL) and methanol (2.0 mL) was added 1N aqueous sodium hydroxide solution (4.0 mL), and the mixture was stirred at 50° C. for 1 hr. The reaction mixture was neutralized with 1N hydrochloric acid (4.0 mL) at room temperature, and 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 (220 mg) as a white amorphous solid.

Workup

extractionextracted with ethyl acetate
washThe extract was washed with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
filtrationAfter silica gel filtration
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-3f90ef55642e40d585a3d820bf2ec7a2
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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