p-Toluenesulfonic acid → HCID 86619321, compound

HRID 1367112Notes

Reaction equation

HRID 1367112 reaction equation
[N:1]1([CH2:6][C@H:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])[CH2:8]2)[CH:5]=[N:4][CH:3]=[N:2]1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30]([OH:33])(=[O:32])=[O:31])=[CH:26][CH:25]=1>C(#N)C.CC(C)=O>[C:24]1([CH3:34])[CH:25]=[CH:26][C:27]([S:30]([OH:33])(=[O:31])=[O:32])=[CH:28][CH:29]=1.[N:1]1([CH2:6][C@H:7]2[CH2:11][CH2:10][C@@H:9]([NH:12][CH2:13][C:14]([N:16]3[CH2:20][C@@H:19]([F:21])[CH2:18][C@H:17]3[C:22]#[N:23])=[O:15])[CH2:8]2)[CH:5]=[N:4][CH:3]=[N:2]1

Participants

5

Reactant 2

HCID 6101p-Toluenesulfonic acidHCID 11623906868771-57-7

Product 1

HCID 86619321HCID 86619321, compoundYield 94.4%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,4S)-1-{2-[(3S,1R)-3-(1H-1,2,4-Triazol-1-ylmethyl)cyclopentyl-amino]acetyl}-4-fluoropyrrolidine-2-carbonitrile (50 g, 156.07 mmol) in acetonitrile (250 ml) was added p-toluenesulfonic acid (47 g, 272.93 mmol) at room temperature under nitrogen atmosphere to result a clear solution. The solution was further stirred for 18 h and the solvent was evaporated under reduced pressure to result a viscous residue. The residue was stirred in dry acetone (200 ml) for 1 h to result a white solid, which was collected by filtration. The residue was washed with acetone (2×50 ml) and dried under vacuum to give 72.6 g of the salt as a white solid; 1H NMR (300 MHz, D2O) δ 1.28-1.50 (m, 2H), 1.68-1.77 (m, 2H), 1.99-2.19 (m, 2H), 2.27-2.69 (m, 3H), 2.38 (s, 3H), 3.53-3.63 (m, 2H), 3.72-4.11 (m, 3H), 4.18 (d, J=7.2 Hz, 2H), 4.95 (d, J=9.3 Hz, 1H), 5.45 (d, J=50.7 Hz, 1H), 7.45 (d, J=6.3 Hz, 2H), 7.71 (d, J=6.3 Hz, 2H), 7.96 (s, 1H), 8.34 (s, 1H).

Workup

  1. customto result a clear solution
  2. customthe solvent was evaporated under reduced pressure
  3. customto result a viscous residue
  4. customto result a white solid, which
  5. filtrationwas collected by filtration
  6. washThe residue was washed with acetone (2×50 ml)
  7. customdried under vacuum

Sources & evidence

ORD record
ord-e73a6c1091f049e189be6a3eaa610a9a
Source dataset
uspto-grants-2011_02
Patent number
US07893103B2

Reaction notes

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