Trifluoroacetic acid → (4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)piperidin-4-yl)methanol

HRID 241649Notes

Reaction equation

HRID 241649 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([CH2:42][OH:43])[CH2:22][CH2:21][N:20](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:3][CH2:2]1.FC(F)(F)C(O)=O>ClCCl>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]4([CH2:42][OH:43])[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:44][C:45]([CH3:48])([CH3:47])[CH3:46])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58513617(4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)-1-tritylpiperidin-4-yl)methanol

Product 1

HCID 58513575(4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)piperidin-4-yl)methanolYield 105.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (4-(1-(cyclopropylmethyl)-2-neopentyl-1H-benzo[d]imidazol-5-ylsulfonyl)-1-tritylpiperidine-4-yl)methanol (STEP F, 300 mg, 0.453 mmol) in dichloromethane (6 mL) was trifluoroacetic acid (2 mL). After 20 min, the mixture was concentrated in vacuo and the residue was diluted with methanol and the solution was filtered through strong cationic exchange column (SCX). The column was washed with 1 mol/L ammonia methanol to wash out the product. The filtrate was concentrated in vacuo to give the title compound (200 mg, quantitative yield).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. additionthe residue was diluted with methanol
  3. filtrationthe solution was filtered through strong cationic exchange column (SCX)
  4. washThe column was washed with 1 mol/L ammonia methanol
  5. washto wash out the product
  6. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-0cce407ac2614684ba8867210ac08daa
Source dataset
uspto-grants-2014_02
Patent number
US08653063B2

Reaction notes

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