1,2-Dichloroethane → n-[(1r)-1-[(4-Chlorophenyl)methyl]-2-(4-{2-[(methylsulfonyl)-amino]phenyl}-piperidyl)-2-oxoethyl]{(1s,3r)-3-[(tert-butoxy)carbonylamino]-cyclopentyl}-carboxamide

Participants

Reaction Steps

The title compound was prepared according to the procedure described in Example 1, Step (f) using (2R)-2-amino-3-(4-chlorophenyl)-1-(4-{2-[(methylsulfonyl)-amino]phenyl}piperidyl)propan-1-one (Example 1, Step g) (471 mg, 1.0 mmol), DIEA (Aldrich) (0.20 mL, 1.0 mmol), (−)-(1S, 3R)—N-Boc-aminocyclopentane-3-carboxylic acid (PepTech Corporation) (344 mg, 1.5 mmol), HOAT (Aldrich) (232 mg, 1.70 mmol) and EDC (Aldrich) (544 mg, 2.84 mmol) in DMF (10 mL). Purification by silica gel chromatography (100% EtOAc) provided the title compound as a white foam (402 mg). MS (ESI, pos. ion) m/z: 647 (M+1); MS (ESI, neg. ion) m/z: 645 (M−1). Calc'd for C32H43ClN4O6S: 647.23.

Provenance & Evidence