Hydrochloric Acid → 3-(2-(((2-(2,2-Dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)propanoic acid

HRID 1049457Notes

Reaction equation

HRID 1049457 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:15]=[CH:14][C:13]([O:16][CH2:17][C:18]2[CH:23]=[C:22]([CH2:24][CH2:25][C:26]([O:28]CC)=[O:27])[CH:21]=[CH:20][N:19]=2)=[CH:12][C:11]=1[CH2:31][C:32]([CH3:35])([CH3:34])[CH3:33].[OH-].[Na+].Cl>C1COCC1.CO>[CH3:33][C:32]([CH3:35])([CH3:34])[CH2:31][C:11]1[CH:12]=[C:13]([O:16][CH2:17][C:18]2[CH:23]=[C:22]([CH2:24][CH2:25][C:26]([OH:28])=[O:27])[CH:21]=[CH:20][N:19]=2)[CH:14]=[CH:15][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 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 117759830Ethyl 3-(2-(((2'-fluoro-5'-methoxy-2-neopentyl-[1,1'-biphenyl]-4-yl)oxy)methyl)pyridin-4-yl)propanoate

Product 1

HCID 1177601313-(2-(((2-(2,2-Dimethylpropyl)-2'-fluoro-5'-methoxybiphenyl-4-yl)oxy)methyl)pyridin-4-yl)propanoic acidYield 73.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 3-(2-(((2′-fluoro-5′-methoxy-2-neopentyl-[1,1′-biphenyl]-4-yl)oxy)methyl)pyridin-4-yl)propanoate (72 mg) in THF (1.5 mL) and methanol (0.75 mL) was added 1N aqueous sodium hydroxide solution (1.5 mL), and the mixture was stirred at room temperature for 20 min. The reaction mixture was neutralized with 1N hydrochloric acid (1.5 mL), and extracted with ethyl acetate. The extract was washed with water and saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure to give the title compound (50 mg) as a white solid.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-1107d7bbedba4c6bba1156b813c1b5b0
Source dataset
uspto-grants-2016_07
Patent number
US09382188B2

Reaction notes

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