Sodium Hydroxide → 3-(3-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-methylphenyl)propanoic acid

HRID 709664Notes

Reaction equation

HRID 709664 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[CH:11]=[CH:12][C:13]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH2:30][CH2:31][C:32]([O:34]CC)=[O:33])[CH:26]=[CH:27][C:28]=2[CH3:29])=[N:14][C:15]=1[CH2:16][C:17]([CH3:20])([CH3:19])[CH3:18].[OH-].[Na+]>CO.C1COCC1.O>[CH3:18][C:17]([CH3:20])([CH3:19])[CH2:16][C:15]1[N:14]=[C:13]([CH2:21][O:22][C:23]2[CH:24]=[C:25]([CH2:30][CH2:31][C:32]([OH:34])=[O:33])[CH:26]=[CH:27][C:28]=2[CH3:29])[CH:12]=[CH:11][C:10]=1[C:3]1[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=1[F:1]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 117760300Ethyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)-4-methylphenyl)propanoate

Product 1

HCID 1177599743-(3-((6-(2,2-Dimethylpropyl)-5-(2-fluoro-5-methoxyphenyl)pyridin-2-yl)methoxy)-4-methylphenyl)propanoic acidYield 92.8%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(3-((5-(2-fluoro-5-methoxyphenyl)-6-neopentylpyridin-2-yl)methoxy)-4-methylphenyl)propanoate (400 mg) in methanol (5.0 mL) and THF (10 mL) was added a solution of sodium hydroxide (333 mg) in water (10 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, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (350 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
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bd05bdb8617a417894bdcbf2317146fc
Source dataset
uspto-grants-2015_11
Patent number
US09181186B2

Reaction notes

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