Trifluoroacetic acid → 4-(2-Amino-2-cyclohexyl-acetyl)-1-methanesulfonyl-octahydro-pyrrolo[3,2-b]pyrrole-3-carboxylic acid (1-phenyl-ethyl)-amide

Participants

Reaction Steps

A solution of 30 (81 mg, 0.14 mmol) in DCM (10 mL) was treated with TFA (3 mL) at 0° C. After 1 h, the reaction mixture was warmed to ambient temperature. After 30 min, the solution was concentrated, diluted with EtOAc, washed with saturated NaHCO3, and brine. The aqueous layers were back-extracted with DCM and the combined organic extracts were dried over anhydrous Na2SO4, filtered and concentrated to afford 31 (60 mg) as an off-white foam. 1H NMR (CDCl3, 300 MHz): δ7.42-7.27 (m, 5H), 5.10-5.01 (m, 1H), 4.57 (d, J=4.5 Hz, 1H), 4.22 (m, 1H), 3.86 (d, J=11.1 Hz, 1H), 3.78 (m, 1H), 3.64-3.46 (m, 2H), 3.19 (m, 1H), 2.96 (s, 3H), 2.62-2.56 (m, 1H), 1.77-1.67 (m, 6H), 1.53 (d, J=6.9 Hz, 3H), 1.19-1.15 (m, 6H) ppm. Mass spectrum, m/z [477.5] (M+H)+.

Provenance & Evidence