Chlorosuccinimide → (R)-2-((2-Chloro-4-(trifluoromethyl)phenyl)amino)-3-methylbutanoic acid

HRID 443464

Reaction equation

HRID 443464 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[Cl:19]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl>[Cl:19][C:7]1[CH:8]=[C:3]([C:2]([F:17])([F:18])[F:1])[CH:4]=[CH:5][C:6]=1[NH:9][C@H:10]([CH:14]([CH3:16])[CH3:15])[C:11]([OH:13])=[O:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13388455N-[4-(trifluoromethyl)phenyl]-D-valine

Product 1

HCID 2316094(R)-2-((2-Chloro-4-(trifluoromethyl)phenyl)amino)-3-methylbutanoic acid

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

To 35 ml of carbon tetrachloride are added 2.81 g (10.0 mmol) of (R)-2-(4-trifluoromethylphenylamino)-3-methylbutanoic acid and 1.33 g (9.96 mmol) of N-chlorosuccinimide, and the mixture is heated to reflux for 1 hour. The mixture is worked up by partition between ether/water. The layers are separated and the aqueous phase is extracted with ether (2×). The combined organic extracts are washed with water and with brine, dried over magnesium sulfate, filtered and evaporated, giving (R)-2-(2-chloro-4-trifluoromethylphenylamino)-3-methylbutanoic acid.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 1 hour
  3. customby partition between ether/water
  4. customThe layers are separated
  5. extractionthe aqueous phase is extracted with ether (2×)
  6. washThe combined organic extracts are washed with water and with brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Sources & evidence

ORD record
ord-5df90869aeeb43d9875121ddb4e74f8e
Source dataset
uspto-grants-1981_04
Patent number
US04260633

Linked notes

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