Trifluoroacetic acid → n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)amino]phenyl}-piperidyl)-2-oxoethyl]((3s, 1r) 3-aminocyclopentyl)carboxamide

Participants

Reaction Steps

To a 50 mL round-bottomed flask was added N-[(1R)-1-[(4-chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}-piperidyl)-2-oxoethyl]{(3S, 1R)-3-[(tert-butoxy)carbonylamino]-cyclopentyl)-carboxamide (Step a) (323 mg, 0.5 mmol) followed by a 50% soln of TFA in CH2Cl2 (20 mL). After stirring for 2 h, the solvent was removed in vacuo. Purification by preparative HPLC [Phenomenex; 5 μm 250×21.2 mm, 5% to 95% CH3CN (0.1% TFA) in H2O (0.1% TFA) over 30 min, then 100% CH3CN (0.1% TFA) for 2 min]provided the title compound (TFA salt) as a white foam (145 mg). MS (ESI, pos. ion) m/z: 547 (M+1); (ESI, neg. ion) 545 (M−1). Calc'd for C27H35ClN4O4S: 546.21. Anal. Calcd for C27H35ClN4O4S.1.2C2HF3O2: C, 51.63; H, 5.49; N, 8.19. Found: C, 51.69; H, 5.49; N, 8.14.

Provenance & Evidence