Ethanol → 3-Amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propanoic acid

HRID 1051360Notes

Reaction equation

HRID 1051360 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[C:10]([F:13])([F:12])[F:11])[CH:5]=O.[C:14]([OH:20])(=[O:19])[CH2:15]C(O)=O.C([O-])(=O)C.[NH4+:25].CCO>CCOCC>[NH2:25][CH:5]([C:4]1[CH:7]=[CH:8][C:9]([C:10]([F:13])([F:12])[F:11])=[C:2]([F:1])[CH:3]=1)[CH2:15][C:14]([OH:20])=[O:19]

Participants

6

Reactant 4

HCID 702EthanolHCID 867Malonic AcidHCID 517165Ammonium AcetateHCID 27375373-Fluoro-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 682942753-Amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propanoic acidYield 31.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 3-fluoro-4-(trifluoromethyl)benzaldehyde (4.8 g, 25 mmol), malonic acid (2.6 g, 25 mmol), ammonium acetate (0.85 g, 50 mmol) and EtOH (30 mL) was heated at 80° C. for 18 h. The reaction was cooled, diluted with Et2O (50 mL) and filtered to afford 2.0 g (16%) of 3-amino-3-(3-fluoro-4-(trifluoromethyl)phenyl)propanoic acid (93) as a white solid which was used without further purification.

Workup

  1. temperatureThe reaction was cooled
  2. filtrationfiltered

Sources & evidence

ORD record
ord-f6ad64d704e5490f92d6335e7e4825e3
Source dataset
uspto-grants-2016_07
Patent number
US09388171B2

Reaction notes

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