Hydrochloric Acid → 3-{2-Methyl-4-[3-methyl-5-(2-pyridin-3-yl-4-trifluoromethyl-phenoxy)-phenoxy]-phenyl}-propionic acid

HRID 1822287Notes

Reaction equation

HRID 1822287 reaction equation
C([O:3][C:4](=[O:39])[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][C:22]=3[C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:17]=[C:16]([CH3:37])[CH:15]=2)=[CH:9][C:8]=1[CH3:38])C.[OH-].[Na+].Cl>C(O)C.O>[CH3:38][C:8]1[CH:9]=[C:10]([O:13][C:14]2[CH:19]=[C:18]([O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:29])([F:30])[F:28])=[CH:23][C:22]=3[C:31]3[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=3)[CH:17]=[C:16]([CH3:37])[CH:15]=2)[CH:11]=[CH:12][C:7]=1[CH2:6][CH2:5][C:4]([OH:39])=[O:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 578941243-{2-Methyl-4-[3-methyl-5-(2-pyridin-3-yl-4-trifluoromethyl-phenoxy)-phenoxy]-phenyl}-propionic acid ethyl ester

Product 1

HCID 112375033-{2-Methyl-4-[3-methyl-5-(2-pyridin-3-yl-4-trifluoromethyl-phenoxy)-phenoxy]-phenyl}-propionic acidYield 110.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A solution of 3-{2-methyl-4-[3-methyl-5-(2-pyridin-3-yl-4-trifluoromethyl-phenoxy)-phenoxy]-phenyl}-propionic acid ethyl ester (0.089, 0.166 mmol) in ethanol (7 mL) is treated with 5 N NaOH (2 mL) and heated to until saponification is completed. The mixture is cooled, and the solvent is removed in vacuo to afford a residue that is neutralized with 1 N HCl. The mixture is diluted with water and extracted with ethyl acetate. The organic layer is dried (Na2SO4), and the solvent is removed in vacuo to afford 0.093 g (100%) of the title compound. 1H NMR (400 MHz, CDCl3); HRMS (ES+) m/z exact mass calculated for C29H24O4F3N 508.1736, found 508.1724.

Workup

  1. temperatureheated to until saponification
  2. temperatureThe mixture is cooled
  3. customthe solvent is removed in vacuo
  4. customto afford a residue that
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer is dried (Na2SO4)
  7. customthe solvent is removed in vacuo

Sources & evidence

ORD record
ord-481e8a46023848d58849ac9062cc6c75
Source dataset
uspto-grants-2009_10
Patent number
US07608639B2

Reaction notes

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