Trifluoroacetic acid → HCID 68675519, compound

HRID 643705Notes

Reaction equation

HRID 643705 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:32])([CH3:31])[C:18]([NH:20][CH2:21][CH2:22][NH:23]C(=O)OC(C)(C)C)=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])[CH2:3][CH2:2]1.F[C:39](F)(F)[C:40](O)=[O:41]>>[NH2:23][CH2:22][CH2:21][N:20]([CH2:39][CH2:40][OH:41])[C:18](=[O:19])[C:17]([S:14]([C:12]1[CH:11]=[CH:10][C:9]2[N:5]([CH2:4][CH:1]3[CH2:3][CH2:2]3)[C:6]([CH2:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[N:7][C:8]=2[CH:13]=1)(=[O:15])=[O:16])([CH3:32])[CH3:31]

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86630623HCID 86630623, compound

Product 1

HCID 68675519HCID 68675519, compoundYield 71%

Procedure

A mixture of 1,1-dimethylethyl {2-[(2-{[1-(cyclopropylmethyl)-2-(2,2-dimethylpropyl)-1H-benzimidazol-5-yl]sulfonyl}-2-methylpropanoyl)amino]ethyl}carbamate (Step A, 217 mg, 0.406 mmol) and trifluoroacetic acid (4 mL) was stirred at room temperature for 1 h. After the mixture was concentrated under reduced pressure, the residue was diluted with dichloromethane. The mixture was washed with 2 mol/L sodium hydroxide aqueous solution and brine, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by HPLC (ODS, gradient elution with acetonitrile/0.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min) to afford the title compound (127 mg, 71%) as an amorphous.

Workup

  1. concentrationAfter the mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with dichloromethane
  3. washThe mixture was washed with 2 mol/L sodium hydroxide aqueous solution and brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe crude product was purified by HPLC (ODS, gradient elution with acetonitrile/0.01% aq. NH3=4:96 to 96:4, by volume; flow rate 40 mL/min)

Sources & evidence

ORD record
ord-d82a55c264e34345af1a4ec0a185e746
Source dataset
uspto-grants-2010_04
Patent number
US07700618B2

Reaction notes

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