Trifluoroacetic acid → HCID 58513611, compound

HRID 241655Notes

Reaction equation

HRID 241655 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][CH:7]([CH2:10][N:11]2[C:15]3[CH:16]=[CH:17][C:18]([S:20]([CH:23]4[CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24]4)(=[O:22])=[O:21])=[CH:19][C:14]=3[N:13]=[C:12]2[CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:6][CH2:5]1)(=[O:3])[CH3:2].FC(F)(F)C(O)=O>ClCCl>[NH:25]1[CH2:26][CH:23]([S:20]([C:18]2[CH:17]=[CH:16][C:15]3[N:11]([CH2:10][CH:7]4[CH2:8][CH2:9][N:4]([C:1](=[O:3])[CH3:2])[CH2:5][CH2:6]4)[C:12]([CH2:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[N:13][C:14]=3[CH:19]=2)(=[O:22])=[O:21])[CH2:24]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58513614HCID 58513614, compound

Product 1

HCID 58513611HCID 58513611, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 3-(1-((1-acetylpiperidin-4-yl)methyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)azetidine-1-carboxylate (STEP C, 220 mg, 0.402 mmol) in dichloromethane (2 mL) was added trifluoroacetic acid (1 mL) at room temperature. After stirring for 40 min, the mixture was concentrated. The residue was diluted with methanol (10 mL) and the solution was filtered through strong cationic exchange column (SCX). The column was washed with 1 mol/L ammonia in methanol (10 mL) to wash out the title compound (176 mg, 98%).

Workup

  1. concentrationthe mixture was concentrated
  2. additionThe residue was diluted with methanol (10 mL)
  3. filtrationthe solution was filtered through strong cationic exchange column (SCX)
  4. washThe column was washed with 1 mol/L ammonia in methanol (10 mL)
  5. washto wash out the title compound (176 mg, 98%)

Sources & evidence

ORD record
ord-b8bd37a72b584c48bcce1b0f18f3a9b9
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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