1,2-Dichloroethane → HCID 71060184, compound

Participants

Reaction Steps

Diisopropylethylamine (0.36 ml, 2.1 mmol) was added in one portion to a stirred solution of 4-(4-tert-butoxycarbonylamino-piperidine-1-sulfonyl)-benzoic acid (0.2 g, 0.52 mmol), EDC (0.2 g, 1.04 mmol) and HOBT (0.16 g, 1.04 mmol) in DCM (5 ml) at room temperature. The mixture was stirred at room temperature for 10 minutes before piperidine (0.07 ml, 0.78 mmol) was added in one portion and stirring continued for 24 hours. After this time the mixture was diluted with DCM (50 ml), washed sequentially with saturated sodium bicarbonate (20 ml), water (20 ml) and brine (20 ml). The organic layer was separated, dired (MgSO4), filtered and concentrated. The resulting residue was purified by flash column chromatography (elution: 0 to 2% MeOH in DCM) to give the title compound (0.17 g, 74% yield) as a white powder. δH (250 MHz, MeOD) 7.89-8.06 (m, 2 H) 7.67-7.82 (m, 2 H) 3.68-3.93 (m, 4 H) 2.54-2.75 (m, 2 H) 2.02 (dd, J=12.94, 3.35 Hz, 2 H) 1.76-1.91 (m, 4 H) 1.56-1.75 (m, 4 H) 1.53 (s, 9 H). Tr=1.94 min m/z (ES+) (M+Na+) 474.

Provenance & Evidence