L-Valine → 2-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acid

HRID 2295411Notes

Reaction equation

HRID 2295411 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1F.[K].[NH2:14][C@H:15]([C:19]([OH:21])=[O:20])[CH:16]([CH3:18])[CH3:17]>[Cl-].C[N+](C)(C)C.S1(CCCC1)(=O)=O.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]([F:12])([F:11])[F:10])[CH:5]=[CH:6][C:7]=1[NH:14][CH:15]([CH:16]([CH3:18])[CH3:17])[C:19]([OH:21])=[O:20]

Participants

7

Reactant 3

HCID 6287L-ValineHCID 157153Benzene, 2-chloro-1-fluoro-4-(trifluoromethyl)-HCID 5462222Potassium

Product 1

HCID 39476432-{[2-Chloro-4-(trifluoromethyl)phenyl]amino}-3-methylbutanoic acid

Reagents, catalysts & solvents 3

HCID 6379Tetramethylammonium chlorideCatalystHCID 962WaterSolventHCID 31347SulfolaneSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 3.04 parts of 3-chloro-4-fluorobenzotrifluoride, 4.5 parts of anhydrous potassium salt of valine, 0.98 parts of tetramethyl-ammonium chloride and 24.0 parts of sulfolane solvent was charged to a reaction vessel, the mixture was heated to 125° C. and maintained thereat for about 16 hours then cooled, diluted with water and acidified to a pH of 1. The aqueous layer was extracted several times with diethyl ether. The ether layer was then washed with copious amounts of water, then dried and concentrated to yield 3.4 parts of 2-(2-chloro-4-trifluoromethylphenyl-amino)-3methylbutanoic acid.

Workup

  1. additionwas charged to a reaction vessel
  2. temperaturemaintained
  3. temperaturefor about 16 hours then cooled
  4. extractionThe aqueous layer was extracted several times with diethyl ether
  5. washThe ether layer was then washed with copious amounts of water
  6. customdried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-16c4139b68a24d618895a5696993dc33
Source dataset
uspto-grants-1984_01
Patent number
US04424396

Reaction notes

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