Chlorosuccinimide → L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-

HRID 1389345Notes

Reaction equation

HRID 1389345 reaction equation
[F:1][C:2]([F:18])([F:17])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@H:10]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12])=[CH:5][CH:4]=1.[Cl:19]N1C(=O)CCC1=O>C1C=CC=CC=1>[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]([C:14]([OH:16])=[O:15])[CH:11]([CH3:13])[CH3:12]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13388454Valine, N-[4-(trifluoromethyl)phenyl]-

Product 1

HCID 156536L-Valine, N-[2-chloro-4-(trifluoromethyl)phenyl]-

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To the m-phenoxybenzyl ester of N-(p-trifluoromethylphenyl)valine (1.57 g) in about 15 ml benzene, with stirring and under nitrogen, is added N-chlorosuccinimide (0.53 g). The reaction mixture is heated to reflux for about 2 hours. The reaction is cooled and partitioned between ether and water. Aqueous phase is back-extracted with ether. The combined ether phases are washed with water and brine, dried over sodium sulfate, filtered and evaporated. The reaction product is put on preparative TLC plates and eluted using 10% ether/hexane to yield the m-phenoxybenzyl ester of N-(2-chloro-4-trifluoromethylphenyl)valine, MS m/e 477.1 (M+).

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for about 2 hours
  3. temperatureThe reaction is cooled
  4. custompartitioned between ether and water
  5. extractionAqueous phase is back-extracted with ether
  6. washThe combined ether phases are washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. washeluted

Sources & evidence

ORD record
ord-5f97046d42fb4d44b670da9005476c09
Source dataset
uspto-grants-1981_01
Patent number
US04243819

Reaction notes

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