Hydrochloric Acid → 3-Cyclopropyl-3-(3-(((2'-fluoro-5'-methoxy-3-(1-methoxy-3,3-dimethylbutyl)biphenyl-4-yl)oxy)methyl)phenyl)propanoic acid

HRID 1049446Notes

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: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])=[CH:21][C:20]=3[CH:34]([O:40][CH3:41])[CH2:35][C:36]([CH3:39])([CH3:38])[CH3:37])[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][O: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])=[CH:21][C:20]=3[CH:34]([O:40][CH3:41])[CH2:35][C:36]([CH3:37])([CH3:38])[CH3:39])[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-3-(1-methoxy-3,3-dimethylbutyl)-[1,1′-biphenyl]-4-yl)oxy)methyl)phenyl)propanoate (385 mg) in ethanol (3.0 mL) was added 1N aqueous sodium hydroxide solution (3.0 mL), and the reaction mixture was stirred at 50° C. for 1 hr. 1N Hydrochloric acid was added, 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 and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (250 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
customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record: ord-a6a532d5f8be4e9685cbc1cb2c6f4814
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382188B2

Reaction notes

Loading…