Triethylamine → 2-(4-Chlorophenyl)-2-(trifluoroacetamido)acetic acid

HRID 1769310Notes

Reaction equation

HRID 1769310 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([C:10]([OH:12])=[O:11])[NH2:9])=[CH:4][CH:3]=1.C(N(CC)CC)C.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23]>CO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([C:10]([OH:12])=[O:11])[NH:9][C:22](=[O:23])[C:21]([F:28])([F:27])[F:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 9794Ethyl trifluoroacetateHCID 587821Benzeneacetic acid, alpha-amino-4-chloro-

Product 1

HCID 199580242-(4-Chlorophenyl)-2-(trifluoroacetamido)acetic acidYield 46.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

A mixture of 2-(p-chlorophenyl)glycine (37.1 g, 0.2 mol) in methanol is treated with triethylamine (20.2 g, 0.2 mol), stirred for 10 minutes, treated dropwise with ethyl trifluoroacetate (35.5 g, 0.25 mol), stirred for 4 days, diluted with methanol and treated with Dowex 50×8-100 ion exchange resin. The reaction mixture is stirred for 10 minutes and filtered. The filter cake is washed with methanol. The filtrates are combined and concentrated in vacuo to afford a yellow solid which is recrystallized from 1,2-dichloroethane to give the title compound as white crystals, 26.4 g (46.8% yield), mp 170°-172° C.

Workup

  1. stirringstirred for 4 days
  2. additiontreated with Dowex 50×8-100 ion exchange resin
  3. stirringThe reaction mixture is stirred for 10 minutes
  4. filtrationfiltered
  5. washThe filter cake is washed with methanol
  6. concentrationconcentrated in vacuo
  7. customto afford a yellow solid which
  8. customis recrystallized from 1,2-dichloroethane

Sources & evidence

ORD record
ord-4b6b155308e44524955befaf00e431e6
Source dataset
uspto-grants-1995_01
Patent number
US05380876

Reaction notes

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