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Trichloroacetyl chloride → N-trichloroacetyl,N-(4-chlorophenyl)valine

HRID 648263
Notes
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Reaction equation

HRID 648263 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[Cl:25][C:26]([Cl:31])([Cl:30])[C:27](Cl)=[O:28].CCOCC.O>CCOCC>[Cl:25][C:26]([Cl:31])([Cl:30])[C:27]([N:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1)[C@H:9]([C:13]([OH:15])=[O:14])[CH:10]([CH3:12])[CH3:11])=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6420Trichloroacetyl chlorideHCID 218852-DimethylaminopyridineHCID 13796078N-(p-chlorophenyl)valineHCID 21584184Diethylether water

Product 1

HCID 57106879N-trichloroacetyl,N-(4-chlorophenyl)valine

Reagents, catalysts & solvents 1

HCID 3283
Diethyl Ether
Solvent
2×

Procedure

To the m-phenoxybenzyl ester of N-(4-chlorophenyl)valine (1.19 mmole) in ether (4.5 ml), under nitrogen, is added dimethylaminopyridine (4.25 mmole) which is cooled in an ice-bath and then trichloroacetyl chloride (3.58 mmole) in ether added slowly. The reaction mixture is heated at 40° for 3 days. The reaction is worked up with ether/water. The aqueous phase is extracted with ether and then the combined ether phases are washed with water and brine and dried over sodium sulfate. The residue is subjected to prep. TLC eluting with 10% ether/hexane to yield the m-phenoxybenzyl ester of N-trichloroacetyl,N-(4-chlorophenyl)valine. MS m/e 553 (M+, 1.8), 183 (100).

Workup

  1. temperatureis cooled in an ice-bath
  2. temperatureThe reaction mixture is heated at 40° for 3 days
  3. extractionThe aqueous phase is extracted with ether
  4. washthe combined ether phases are washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. washTLC eluting with 10% ether/hexane

Sources & evidence

ORD record
ord-72bbdc80c9cf49f7981d53888e8f0fd7
Source dataset
uspto-grants-1983_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04411912

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes