Trifluoroacetic acid → (3-Benzyl-2-oxoimidazolidin-1-yl)acetic acid

HRID 23560Notes

Reaction equation

HRID 23560 reaction equation
[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][N:3]1[CH2:14][C:15]([O:17]C(C)(C)C)=[O:16].FC(F)(F)C(O)=O>ClCCl>[O:1]=[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:5][CH2:4][N:3]1[CH2:14][C:15]([OH:17])=[O:16]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 22574612Tert-butyl 2-(2-oxo-3-benzylimidazolidinyl)acetate

Product 1

HCID 3238717(3-Benzyl-2-oxoimidazolidin-1-yl)acetic acidYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 2-(2-oxo-3-benzylimidazolidinyl)acetate (2.51 g, 8.64 mmol) in dichloromethane (15 ml) was added trifluoroacetic acid (10 ml). After stirring the mixture at room temperature for 1 hour, the solvent was removed under reduced pressure. The oily residue was crystallized by treating with ethyl acetate and filtered off to give 2-(2-oxo-3-benzylimidazolidinyl)acetic acid (1.56 g).

Workup

  1. customthe solvent was removed under reduced pressure
  2. customThe oily residue was crystallized
  3. additionby treating with ethyl acetate
  4. filtrationfiltered off

Sources & evidence

ORD record
ord-b1dc982ba59e4cffb50eafd6026107d9
Source dataset
uspto-grants-2005_02
Patent number
US06852744B2

Reaction notes

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