Hydrochloric Acid → (3-(((2-(2,2-Dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)phenoxy)acetic acid

HRID 1049402Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=2)[O:26][CH2:27][C:28]([O:30]CC)=[O:29])=N[C:15]=1[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].[OH-].[Na+].Cl.[CH2:39]1COCC1>CO>[CH3:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]1[CH:39]=[C:13]([O:21][CH2:22][C:23]2[CH:24]=[C:25]([CH:33]=[CH:34][CH:35]=2)[O:26][CH2:27][C:28]([OH:30])=[O:29])[CH:12]=[CH:11][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of ethyl 2-(3-(((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)oxy)methyl)phenoxy)acetate (102 mg) in THF (3.0 mL) and methanol (3.0 mL) was added 1N aqueous sodium hydroxide solution (0.97 mL), and the mixture was stirred at 80° C. for 30 min. To the reaction mixture was added 1N hydrochloric acid (1.0 mL), 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 (83 mg) as a colorless oil.

Workup

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

Sources & evidence

ORD record: ord-d8555ae22ac6401fbadad080ee9302d1
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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