p-Toluenesulfonic acid → HCID 86619321, compound

Participants

Reaction Steps

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).

Provenance & Evidence