Trifluoroacetic acid → HCID 178506537, compound

HRID 1625529Notes

Reaction equation

HRID 1625529 reaction equation
C(OC([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C:13]1[NH:17][C:16]2[CH:18]=[CH:19][C:20]([I:22])=[CH:21][C:15]=2[N:14]=1)=O)(C)(C)C.[C:23]([OH:29])([C:25]([F:28])([F:27])[F:26])=[O:24]>C(Cl)Cl>[OH:29][C:23]([C:25]([F:28])([F:27])[F:26])=[O:24].[I:22][C:20]1[CH:19]=[CH:18][C:16]2[NH:17][C:13]([C@@H:9]3[CH2:10][CH2:11][CH2:12][NH:8]3)=[N:14][C:15]=2[CH:21]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178451904HCID 178451904, compound

Product 1

HCID 178506537HCID 178506537, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirring mixture of (S)-2-(5-Iodo-1H-benzoimidazol-2-yl)-pyrrolidine-1-carboxylic acid tert-butyl ester (20 g, 48 mmol) in CH2Cl2 (200 mL) at 0° C. is added TFA (200 mL). The reaction mixture is stirred at room temperature for 2 hours and concentrated in vacuum. The residue is dissolved in CH2Cl2 and saturated aqueous NaHCO3, the organic layer is washed with saturated aqueous NaHCO3, dried over sodium sulfate and concentrated in vacuum to afford (S)-5-iodo-2-(pyrrolidin-2-yl)-1H-benzo[d]imidazole-TFA salt (12 g).

Workup

  1. concentrationconcentrated in vacuum
  2. dissolutionThe residue is dissolved in CH2Cl2
  3. washsaturated aqueous NaHCO3, the organic layer is washed with saturated aqueous NaHCO3
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuum

Sources & evidence

ORD record
ord-80b7c582cc9e4e77b12ca5242de16adf
Source dataset
uspto-grants-2014_07
Patent number
US08779156B2

Reaction notes

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