Sodium Hydroxide → 3-Cyclopropyl-3-(2-(((5-(2,2-dimethylpropyl)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)oxy)methyl)pyridin-4-yl)propanoic acid

HRID 1049478Notes

Reaction equation

HRID 1049478 reaction equation
[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([C:30]4[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=4[F:38])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:28])[CH3:27])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([O:8]CC)=[O:7])[CH2:3][CH2:2]1.[OH-].[Na+]>C1COCC1.CO>[CH:1]1([CH:4]([C:11]2[CH:16]=[CH:15][N:14]=[C:13]([CH2:17][O:18][C:19]3[CH:20]=[N:21][C:22]([C:30]4[CH:35]=[C:34]([O:36][CH3:37])[CH:33]=[CH:32][C:31]=4[F:38])=[C:23]([CH2:25][C:26]([CH3:29])([CH3:27])[CH3:28])[CH:24]=3)[CH:12]=2)[CH2:5][C:6]([OH:8])=[O:7])[CH2:2][CH2:3]1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 117760133Ethyl 3-cyclopropyl-3-(2-(((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)oxy)methyl)pyridin-4-yl)propanoate

Product 1

HCID 1177599043-Cyclopropyl-3-(2-(((5-(2,2-dimethylpropyl)-6-(2-fluoro-5-methoxyphenyl)pyridin-3-yl)oxy)methyl)pyridin-4-yl)propanoic acidYield 95.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-cyclopropyl-3-(2-(((6-(2-fluoro-5-methoxyphenyl)-5-neopentylpyridin-3-yl)oxy)methyl)pyridin-4-yl)propanoate (182 mg) in THF (2.0 mL) and methanol (1.0 mL) was added 1N aqueous sodium hydroxide solution (2.0 mL), and the mixture was stirred at room temperature for 30 min. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (methanol/ethyl acetate) to give the title compound (164 mg) as a white amorphous solid.

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe residue was purified by silica gel column chromatography (methanol/ethyl acetate)

Sources & evidence

ORD record
ord-0a03b79ac3c04c2e8abbe152f6e51de8
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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