Trifluoroacetic acid → (6-Cyano-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetic acid

HRID 1631964Notes

Reaction equation

HRID 1631964 reaction equation
C([O:5][C:6]([CH:8]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[N:9]1[C:13]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=2[N:11](C(OC(C)(C)C)=O)[C:10]1=[O:27])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[C:18]([C:15]1[CH:16]=[CH:17][C:12]2[NH:11][C:10](=[O:27])[N:9]([CH:8]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:6]([OH:7])=[O:5])[C:13]=2[CH:14]=1)#[N:19]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66755109tert-Butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydro-benzimidazole-1-carboxylate2×

Product 1

HCID 24900960(6-Cyano-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate 695 mg (1.55 mmol) of tert-butyl 3-(tert-butoxycarbonylphenylmethyl)-5-cyano-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (VIIc) were dissolved in dichloromethane (30 ml) and, while stirring at room temperature, trifluoroacetic acid (20 ml) was added. The reaction solution was stirred for 2 h and then the solvent and excess trifluoroacetic acid were removed in vacuo. The residue was taken up again in toluene, concentrated in vacuo and then dried in vacuo. Yield: 449 mg (99%) of white solid

Workup

  1. stirringThe reaction solution was stirred for 2 h
  2. customthe solvent and excess trifluoroacetic acid were removed in vacuo
  3. concentrationconcentrated in vacuo
  4. customdried in vacuo

Sources & evidence

ORD record
ord-c8e0a6c536a647329054f8aebac43f13
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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