Tridecanoic acid → HCID 15479956, compound

Participants

Reaction Steps

(S)-(6-{[1-(1-Tridecanoyl-piperidin-2-yl)-methanoyl]-amino}-hexyl)-carbamic acid tert-butyl ester was obtained by treating a solution of {6-[(1-piperidin-2-yl-methanoyl)-amino]hexyl}-carbamic acid tert-butyl ester in DCM (100 mL) with tridecanoic acid (2.36 g, 1.1 equiv.) in the presence of HATU (5.0 g, 1.3 equiv.) and DIEA (4.2 mL, 2.4 equiv.). After 2 hours of stirring at rt the reaction was judged to be complete by tlc monitoring. DCM was added (50 mL) and the reaction mixture was washed 3 times with citric acid (0.5 M). 3 times with an aqueous saturated solution of NaHCO3 and with brine. Drying over Na2SO4, evaporation in vacuo gave a residue which was purified via flash chromatography (SiO2) using EtOAc:chexanes (6:4) as eluant. (S)-(6-{[1-(1-Tridecanoyl-piperidin-2-yl)-methanoyl]-amino}-hexyl)-carbamic acid tert-butyl ester (4.6 g) was obtained as a yellow oil in a 87% yield.

Provenance & Evidence