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

HRID 1049453Notes

Reaction equation

HRID 1049453 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]=[C:21]([C:34]4[CH:39]=[CH:38][C:37]([C:40]([F:43])([F:42])[F:41])=[CH:36][CH:35]=4)[C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[CH:23][CH:24]=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][O:18][C:19]3[CH:20]=[C:21]([C:34]4[CH:35]=[CH:36][C:37]([C:40]([F:43])([F:41])[F:42])=[CH:38][CH:39]=4)[C:22]([C:25]4[CH:30]=[C:29]([O:31][CH3:32])[CH:28]=[CH:27][C:26]=4[F:33])=[CH:23][CH:24]=3)[CH:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117760114Ethyl 3-cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4''-(trifluoromethyl)-1,1':2',1''-terphenyl-4'-yl)oxy)methyl)phenyl)propanoate

Product 1

HCID 1177600363-Cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4''-(trifluoromethyl)-1,1':2',1''-terphenyl-4'-yl)oxy)methyl)phenyl)propanoic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of ethyl 3-cyclopropyl-3-(3-(((2-fluoro-5-methoxy-4″-(trifluoromethyl)-1,1′:2′,1″-terphenyl-4′-yl)oxy)methyl)phenyl)propanoate (92 mg) in ethanol (3.0 mL) was added 2N aqueous sodium hydroxide solution (0.16 mL), and the mixture was stirred at 50° C. for 15 hr. To the reaction mixture was added 1N hydrochloric acid, 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 (85 mg) as a white solid.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-442ccd267e954df8bd82a3155e4ecb1f
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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