Hydrochloric Acid → 3-[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoic acid

HRID 623891Notes

Reaction equation

CO.[F:3][C:4]1[CH:5]=[C:6]([C:27]2[C:28]([CH3:42])=[CH:29][C:30]([O:33][CH2:34][C:35]([CH3:41])([CH3:40])[C:36]([O:38]C)=[O:37])=[N:31][CH:32]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:26])([CH3:25])[CH3:24])[CH:12]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:14]=1.[OH-].[Na+].Cl>C(OCC)(=O)C.O1CCCC1>[F:3][C:4]1[CH:5]=[C:6]([C:27]2[C:28]([CH3:42])=[CH:29][C:30]([O:33][CH2:34][C:35]([CH3:40])([CH3:41])[C:36]([OH:38])=[O:37])=[N:31][CH:32]=2)[CH:7]=[CH:8][C:9]=1[C:10]1[N:11]([CH2:19][O:20][CH2:21][CH2:22][Si:23]([CH3:24])([CH3:26])[CH3:25])[CH:12]=[C:13]([C:15]([F:18])([F:16])[F:17])[N:14]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Methanol (3.0 mL) and tetrahydrofuran (3.0 mL) were added to methyl 3-[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoate (660 mg), and after adding 2N aqueous sodium hydroxide solution (4.0 mL) to the mixture, the resulting mixture was stirred at 50° C. for 2 hours. Ethyl acetate was added to the reaction mixture, and the mixture was neutralized by 2N hydrochloric acid. The organic layer was separated, washed with a saturated brine, and concentrated under reduced pressure to obtain 3-[(5-{3-fluoro-4-[4-(trifluoromethyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl]phenyl}-4-methylpyridin-2-yl)oxy]-2,2-dimethylpropanoic acid (721 mg).

Workup

customThe organic layer was separated
washwashed with a saturated brine
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-be473516342b45f1af196272436f2bc3
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09302996B2

Reaction notes

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