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

HRID 1631968Notes

Reaction equation

HRID 1631968 reaction equation
C([O:5][C:6]([CH:8]([N:16]1[C:20]2[CH:21]=[C:22]([Cl:25])[CH:23]=[CH:24][C:19]=2[N:18](C(OC(C)(C)C)=O)[C:17]1=[O:33])[CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7])(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[Cl:25][C:22]1[CH:23]=[CH:24][C:19]2[NH:18][C:17](=[O:33])[N:16]([CH:8]([CH2:9][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:6]([OH:7])=[O:5])[C:20]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 24901094HCID 24901094, compound

Product 1

HCID 249010952-(6-Chloro-2-oxo-2,3-dihydrobenzimidazol-1-yl)-3-phenylpropionic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

950 mg (2.01 mmol) of tert-butyl 3-(1-tert-butoxycarbonyl-2-phenylethyl)-5-chloro-2-oxo-2,3-dihydrobenzimidazole-1-carboxylate (VIIh) were dissolved in dichloromethane (10 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: 609 mg (96%) 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-41340e1d3f8048c09c02a71bab0afb22
Source dataset
uspto-grants-2014_07
Patent number
US08791148B2

Reaction notes

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