1,4-Dioxane → HCID 66996529, compound

Participants

Reaction Steps

In a 4 mL vial tert-butyl methyl((S)-4-methyl-1-oxo-1-((3aR,4S,6aS)-2-(2-(trifluoromethyl)phenyl)octahydrocyclopenta[c]pyrrol-4-ylamino)pentan-2-yl)carbamate from Step 3 (40 mg, 0.080 mmol) was dissolved in 4 N HCl in 1,4-dioxane (1 mL, 4.00 mmol). An oil slowly gummed out of the solution. The reaction was stirred at ambient temperature for 18 hours, and then the solvent was removed under a stream of nitrogen. The crude material was purified using a 4 g silica gel cartridge with 1-10% methanol (2 N ammonia)/dichloromethane to give N2-methyl-N-{(3aR,4S,6aS)-2-[2-(trifluoromethyl)phenyl]octahydrocyclopenta[c]pyrrol-4-yl}-L-leucinamide: 1H NMR (400 MHz, pyridine-d5) δ ppm 8.28 (d, J=5.2, 1H), 7.66 (d, J=7.8, 1H), 7.46 (t, J=7.4, 1H), 7.27 (d, J=8.3, 1H), 7.11 (t, J=7.7, 1H), 4.56-4.46 (m, 1H), 3.47 (d, J=9.3, 1H), 3.30-3.23 (m, 1H), 3.16-3.09 (m, 1H), 3.02-2.91 (m, 2H), 2.68 (dd, J=14.4, 10.2, 2H), 2.45 (s, 3H), 2.20 (dd, J=11.1, 5.9, 1H), 2.00-1.86 (m, 2H), 1.79-1.70 (m, 1H), 1.69-1.54 (m, 3H), 0.93 (d, J=6.5, 3H), 0.86 (d, J=6.5, 3H); MS (ESI+) m/z 398 (M+H)+.

Provenance & Evidence