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Sodium Hydroxide → 3-(3-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxyphenyl)propanoic acid

HRID 709679
Notes
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Reaction equation

HRID 709679 reaction equation
[CH3:1][C:2]([CH3:37])([CH3:36])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:20][CH2:21][C:22]([O:24]CC)=[O:23])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)[CH:7]=[CH:6][C:5]=1[C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[F:35].[OH-].[Na+]>CO.C1COCC1>[CH3:1][C:2]([CH3:37])([CH3:36])[CH2:3][C:4]1[N:9]=[C:8]([CH2:10][O:11][C:12]2[CH:13]=[C:14]([CH2:20][CH2:21][C:22]([OH:24])=[O:23])[CH:15]=[C:16]([O:18][CH3:19])[CH:17]=2)[CH:7]=[CH:6][C:5]=1[C:27]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[CH:29][C:28]=1[F:35]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117760128Ethyl 3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxyphenyl)propanoate

Product 1

HCID 1177600193-(3-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxyphenyl)propanoic acidYield 75%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent
HCID 8028
Tetrahydrofuran
Solvent

Procedure

To a solution of ethyl 3-(3-((6-(2,2-dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-5-methoxyphenyl)propanoate (450 mg) in methanol (4.0 mL) and THF (8.0 mL) was added 1N aqueous sodium hydroxide solution (8.0 mL), and the mixture was stirred at room temperature for 15 hr. The reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid was added to the residue to adjust to pH<4. The reaction mixture was extracted with ethyl acetate, and the extract was washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give the title compound (319 mg) as a yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure, and 1N hydrochloric acid
  2. additionwas added to the residue
  3. extractionThe reaction mixture was extracted with ethyl acetate
  4. washthe extract was washed with saturated brine
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-c4298e5ced284065a3baf6adfd2e63fa
Source dataset
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09181186B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes