Trifluoroacetic acid → (6-Chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)acetic acid

HRID 1631950Notes

Reaction equation

HRID 1631950 reaction equation
C([O:5][C:6]([CH2:8][N:9]1[C:13]2[CH:14]=[C:15]([Cl:18])[CH:16]=[CH:17][C:12]=2[N:11](C(OC(C)(C)C)=O)[C:10]1=[O:26])=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]2[NH:11][C:10](=[O:26])[N:9]([CH2:8][C:6]([OH:7])=[O:5])[C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66754580Tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

Product 1

HCID 10704472(6-Chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.92 g (5.02 mmol) of tert-butyl 3-tert-butoxycarbonylmethyl-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (VIIg) were dissolved in dichloromethane (40 ml) and, while stirring at room temperature, trifluoroacetic acid (15 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: 1.50 g (100%) 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-d8bd0ad1bb5542958ca97e86de4241cd
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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