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

HRID 1631954Notes

Reaction equation

HRID 1631954 reaction equation
C([O:5][C:6]([CH:8]([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[N:9]1[C:13]2[CH:14]=[C:15]([I: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>[I:18][C:15]1[CH:16]=[CH:17][C:12]2[NH:11][C:10](=[O:26])[N:9]([CH:8]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)[C:6]([OH:7])=[O:5])[C:13]=2[CH:14]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 66754745Tert-butyl 3-(tert-butoxycarbonylphenylmethyl)-5-iodo-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate

Product 1

HCID 66755373(6-Iodo-2-oxo-2,3-dihydrobenzimidazol-1-yl)phenylacetic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1.50 g (2.73 mmol) of tert-butyl 3-(tert-butoxycarbonylphenylmethyl)-5-iodo-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (XIIb) were dissolved in dichloromethane (16 ml) and, while stirring at room temperature, trifluoroacetic acid (10 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: 1.10 g (100%) of yellow 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-8990dfa2a3a443f6a856733fff5b2458
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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