L-Valine → 2-(4-Trifluoromethylphenylamino)-3-methylbutanoic acid

HRID 2295408Notes

Reaction equation

HRID 2295408 reaction equation
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][CH:3]=1.[NH2:12][C@H:13]([C:17]([OH:19])=[O:18])[CH:14]([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].S1(CCCC1)(=O)=O>[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[F:9][C:8]([F:11])([F:10])[C:5]1[CH:6]=[CH:7][C:2]([NH:12][CH:13]([CH:14]([CH3:16])[CH3:15])[C:17]([OH:19])=[O:18])=[CH:3][CH:4]=1

Participants

6

Reactant 4

HCID 6287L-ValineHCID 11430Potassium CarbonateHCID 31347SulfolaneHCID 67873Benzene, 1-fluoro-4-(trifluoromethyl)-

Product 1

HCID 133884532-(4-Trifluoromethylphenylamino)-3-methylbutanoic acidYield 53%

Reagents, catalysts & solvents 1

HCID 67553Tetrabutylammonium IodideCatalyst

Conditions

Temperature
140 °C

Procedure

A mixture of 80 parts of p-fluorobenzotrifluoride, 114 parts of valine, 135 parts of potassium carbonate, 65 parts of tetra(n-butyl)ammonium iodide, and 630 parts of sulfolane was placed in a pressure reactor. The reactor was degassed, placed under an argon atmosphere, sealed, and then heated and maintained at about 140° C. for about 18 hours. Analysis of the reaction product indicated 53.0% yield of 2-(4-trifluoromethylphenylamino)-3-methylbutanoic acid, based on p-fluorobenzotrifluoride starting materials.

Workup

  1. customwas placed in a pressure reactor
  2. customThe reactor was degassed
  3. customsealed
  4. temperatureheated

Sources & evidence

ORD record
ord-bbc2ddb48bb048ce8e565eef2fd06c81
Source dataset
uspto-grants-1984_01
Patent number
US04424396

Reaction notes

Loading…