Trifluoroacetic acid → HCID 69074486, compound

HRID 1510243Notes

Reaction equation

HRID 1510243 reaction equation
[C:1]1([C@H:7]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=3)=[CH:21][CH:20]=2)=[O:17])[C:8]([O:10]C(C)(C)C)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34]>ClCCl>[F:31][C:32]([F:37])([F:36])[C:33]([OH:35])=[O:34].[C:1]1([C@H:7]([NH:15][C:16]([NH:18][C:19]2[CH:24]=[CH:23][C:22]([C:25]3[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=3)=[CH:21][CH:20]=2)=[O:17])[C:8]([OH:10])=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86629754HCID 86629754, compound

Product 1

HCID 69074486HCID 69074486, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

The solution of tert-butyl (2S)-phenyl[({[4-(4-pyridinyl)phenyl]amino}carbonyl)amino]acetate (50.0 mg) in dichloromethane (1.0 mL) and trifluoroacetic acid (954 μL) was stand at ambient temperature for 2 hours. The resulting mixture was concentrated in vacuo and the residue was diluted with chloroform (2 mL), then concentrated. To the residue was added ethyl acetate (2.0 mL) and the precipitated solid was collected by filtration, then washed with ethyl acetate (2.0 mL) to give (2S)-phenyl[({[4-(4-pyridinyl)phenyl]amino}carbonyl)amino]acetic acid trifluoroacetate (39 mg) as off-white crystals.

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionthe residue was diluted with chloroform (2 mL)
  3. concentrationconcentrated
  4. additionTo the residue was added ethyl acetate (2.0 mL)
  5. filtrationthe precipitated solid was collected by filtration
  6. washwashed with ethyl acetate (2.0 mL)

Sources & evidence

ORD record
ord-7b8aa8b8999f462fa54e8b49669cee76
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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