Hydrochloric Acid → 3-(2-(((2-(2-Cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)-3-cyclopropylpropanoic acid

HRID 1049490Notes

Reaction equation

HRID 1049490 reaction equation
[C:1]([C:3]([CH3:39])([CH3:38])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[C:17]([CH:19]([CH:26]3[CH2:28][CH2:27]3)[CH2:20][C:21]([O:23]CC)=[O:22])[CH:16]=[CH:15][N:14]=2)[CH:8]=[CH:7][C:6]=1[C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1[F:37])#[N:2].[OH-].[Na+].Cl>C(O)C>[C:1]([C:3]([CH3:39])([CH3:38])[CH2:4][C:5]1[CH:10]=[C:9]([O:11][CH2:12][C:13]2[CH:18]=[C:17]([CH:19]([CH:26]3[CH2:27][CH2:28]3)[CH2:20][C:21]([OH:23])=[O:22])[CH:16]=[CH:15][N:14]=2)[CH:8]=[CH:7][C:6]=1[C:29]1[CH:34]=[C:33]([O:35][CH3:36])[CH:32]=[CH:31][C:30]=1[F:37])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117759958Ethyl 3-(2-(((2-(2-cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)-3-cyclopropylpropanoate

Product 1

HCID 1177600393-(2-(((2-(2-Cyano-2-methylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)-3-cyclopropylpropanoic acidYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 3-(2-(((2-(2-cyano-2-methylpropyl)-2′-fluoro-5′-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)-3-cyclopropylpropanoate (234 mg) in ethanol (5.0 mL) was added 2N aqueous sodium hydroxide solution (0.44 mL), and the mixture was stirred at room temperature for 16 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 (220 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-7c8de256af2244869c642c603cbf2019
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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