Hydrochloric Acid → 4,4,4-Trifluoro-3-methyl-2-(4-{[2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]methyl}phenyl)-butanoic acid

HRID 877252Notes

Reaction equation

HRID 877252 reaction equation
[F:1][C:2]([F:30])([F:29])[CH:3]([CH3:28])[CH:4]([C:10]1[CH:15]=[CH:14][C:13]([CH2:16][N:17]2[CH:22]=[C:21]([C:23]([F:26])([F:25])[F:24])[CH:20]=[CH:19][C:18]2=[O:27])=[CH:12][CH:11]=1)[C:5]([O:7]CC)=[O:6].CO.[OH-].[Na+].Cl>C1COCC1.O>[F:30][C:2]([F:1])([F:29])[CH:3]([CH3:28])[CH:4]([C:10]1[CH:11]=[CH:12][C:13]([CH2:16][N:17]2[CH:22]=[C:21]([C:23]([F:25])([F:26])[F:24])[CH:20]=[CH:19][C:18]2=[O:27])=[CH:14][CH:15]=1)[C:5]([OH:7])=[O:6]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 58136589Ethyl 4,4,4-trifluoro-3-methyl-2-(4-{[2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]methyl}phenyl)butanoate

Product 1

HCID 581364994,4,4-Trifluoro-3-methyl-2-(4-{[2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]methyl}phenyl)-butanoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

2.80 g (6.43 mmol) of ethyl 4,4,4-trifluoro-3-methyl-2-(4-{[2-oxo-5-(trifluoromethyl)pyridin-1(2H)-yl]methyl}phenyl)butanoate were dissolved in 18.2 ml each of THF, methanol and water, and 51.5 ml (128.6 mmol) of 10% strength aqueous sodium hydroxide solution were added. The mixture was stirred at RT overnight. The reaction mixture was then diluted with water, acidified with 1 N hydrochloric acid and extracted with ethyl acetate. The organic phase was dried over sodium sulfate and concentrated. This gave 2.82 g of product, which was used without further purification.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated
  4. customThis gave 2.82 g of product, which was used without further purification

Sources & evidence

ORD record
ord-4456782a31904308b36f1372ebed19f7
Source dataset
uspto-grants-2015_03
Patent number
US08987256B2

Reaction notes

Loading…