2-Dimethylaminopyridine → Hexadecanoic acid (2-oxo-4-pentadec-1-enyl-[1,3]dioxan-5-yl)-amide

Participants

Reaction Steps

N-palmitoylsphingosine (C16-ceramide, 1.61 g, 3 mmol) was dissolved in dry THF (100 ml) with heating. The clear solution was brought to room temperature and N,N′-disuccinimidyl carbonate (1.92 g, 7.5 mmol) was added. Dimethylaminopyridine (DMAP 0.81 g, 7.5 mmol) was added with stirring and the reaction further stirred for 16 hours. The solvent was removed under reduced pressure and the residue was re-crystallized from n-heptane yielding 1.3 g (68%) of disuccinimidylceramidyl carbonate as white powder m.p. 73-76° C.

Provenance & Evidence