Sodium Hydroxide → 2-acetamido-3-[4-(trifluoromethyl)phenyl]propanoic Acid

HRID 1425919Notes

Reaction equation

HRID 1425919 reaction equation
[C:1]([NH:4][C:5]([CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][CH:18]=1)(C(OCC)=O)[C:6]([O:8]CC)=[O:7])(=[O:3])[CH3:2].[OH-].[Na+]>CC(C)=O>[C:1]([NH:4][CH:5]([CH2:16][C:17]1[CH:18]=[CH:19][C:20]([C:23]([F:24])([F:25])[F:26])=[CH:21][CH:22]=1)[C:6]([OH:8])=[O:7])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 3120443HCID 3120443, compound

Product 1

HCID 108499842-acetamido-3-[4-(trifluoromethyl)phenyl]propanoic AcidYield 75%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of diethyl 2-acetamido-2-(4-(trifluoromethyl)benzyl)malonate (LXII) (theoretical 0.125 mole) in acetone (400 mL) was added aq. 2 M NaOH (400 mL). The mixture was refluxed overnight before the solvent was removed under reduced pressure. The residue was taken up in water, washed with hexane (3×), acidified to pH=1 and filtered to produce 2-acetamido-3-(4-(trifluoromethyl)phenyl)propanoic acid (LXIII) as a white solid (25.8 g, 93.7 mmol, 75% yield after two steps).

Workup

  1. temperatureThe mixture was refluxed overnight before the solvent
  2. customwas removed under reduced pressure
  3. washwashed with hexane (3×)
  4. filtrationfiltered

Sources & evidence

ORD record
ord-b5af7094fe0b426288367ac3d913580f
Source dataset
uspto-grants-2015_01
Patent number
US08933018B2

Reaction notes

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