Hydrochloric Acid → 2-Ethoxy-3-(4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl)propanoic acid

HRID 1816554Notes

Reaction equation

HRID 1816554 reaction equation
[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([C:19]([NH:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[O:20])[CH:12]=1)[C:5]([O:7]CC)=[O:6])[CH3:2].[OH-].[Na+].Cl>C(O)C>[CH2:1]([O:3][CH:4]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([C:19]([NH:21][CH2:22][C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:27][CH:28]=2)=[O:20])[CH:12]=1)[C:5]([OH:7])=[O:6])[CH3:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 10906522Ethyl 2-ethoxy-3-(4-methoxy-3-(([4-(trifluoromethyl)benzyl)amino)carbonyl)phenyl)propanoate

Product 1

HCID 129676842-Ethoxy-3-(4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl)propanoic acidYield 76.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.25 g of ethyl 2-ethoxy-3-(4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl)propanoate was dissolved in 7 ml ethanol, and 3 ml of 1 N sodium hydroxide was added, and the mixture was stirred at room temperature for 14 hours. The reaction mixture was ice-cooled, neutralized with 1N hydrochloric acid, and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was evaporated, to give 0.18 g of 2-ethoxy-3-(4-methoxy-3-({[4-(trifluoromethyl)benzyl]amino}carbonyl)phenyl)propanoic acid.

Workup

  1. temperaturecooled
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated

Sources & evidence

ORD record
ord-acc5576c845b489eb5a31af35463a6da
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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