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

HRID 892629Notes

Reaction equation

HRID 892629 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-8fd91a602874429bbe98e78d298f03c9
Source dataset
uspto-grants-1992_06
Patent number
US05118816

Reaction notes

Loading…