Trifluoroacetic acid → {3-[5-carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid

HRID 896321Notes

Reaction equation

HRID 896321 reaction equation
C([O:5][C:6](=[O:36])[CH2:7][N:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:17][C:18]2[N:22]([CH2:23][CH2:24][CH:25]([CH3:27])[CH3:26])[C:21]3[CH:28]=[CH:29][C:30]([C:32](=[NH:34])[NH2:33])=[CH:31][C:20]=3[N:19]=2)[C:9]1=[O:35])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[C:32]([C:30]1[CH:29]=[CH:28][C:21]2[N:22]([CH2:23][CH2:24][CH:25]([CH3:26])[CH3:27])[C:18]([CH2:17][N:10]3[C:11]4[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=4[N:8]([CH2:7][C:6]([OH:36])=[O:5])[C:9]3=[O:35])=[N:19][C:20]=2[CH:31]=1)(=[NH:33])[NH2:34]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 20814118{3-[5-carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester

Product 1

HCID 20814025{3-[5-carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acidYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

{3-[5-Carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid tert-butyl ester (1.0 g, 2.0 mmol) was dissolved in CH2Cl2 (50 ml) treated with TFA (3 ml) and stirred for 48 h. The solvent was removed and the residue triturated with EtOAc to give 850 mg (98%) of {3-[5-Carbamimidoyl-1-(3-methyl-butyl)-1H-benzoimidazol-2-ylmethyl]-2-oxo-2,3-dihydro-benzoimidazol-1-yl}-acetic acid as a with solid.

Workup

  1. customThe solvent was removed
  2. customthe residue triturated with EtOAc

Sources & evidence

ORD record
ord-4864e0f0f5004de7ad857beaa9e3ec93
Source dataset
uspto-grants-2005_07
Patent number
US06919331B2

Reaction notes

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