Hydrochloric Acid → 3-Cyclopropyl-3-(3-(((2-(2,2-dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)sulfanyl)methyl)phenyl)propanoic acid

HRID 1049436Notes

Reaction equation

[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][S:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:20]=3)[CH:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>C(O)C>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH2:17][S:18][C:19]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[C:21]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH:20]=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-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)thio)methyl)phenyl)propanoate (136 mg) in ethanol (2.5 mL) was added 2N aqueous sodium hydroxide solution (634 μL) at room temperature, and the mixture was stirred at 50° C. for 2 hr. The reaction mixture was cooled to 0° C., neutralized with 1N hydrochloric acid, and extracted with ethyl acetate. The extract was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give the title compound (56 mg) as a white amorphous solid.

Workup

temperatureThe reaction mixture was cooled to 0° C.
extractionextracted with ethyl acetate
dry with materialThe extract was dried over anhydrous sodium sulfate
customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record: ord-1e2e37564ae04d31a98e25069f4dba7a
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

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