Heptadecanoic Acid N-HydroxysucciniMide Ester synthesis

Yield:201472-73-3 66%

Reaction Conditions:

Stage #1: heptadecanoic acidwith dicyclohexyl-carbodiimide in tetrahydrofuran at 20; for 0.166667 h;
Stage #2: 1-hydroxy-pyrrolidine-2,5-dione in tetrahydrofuran at 20; for 22.5 h;

Steps:

Synthesis of 2,5-dioxopyrrolidin-1-yl tetradecanoate (12)

General procedure: Tetradecanoic acid [3.00 g (13.1 mmol)] and 3.24 g of N,N′-dicyclohexylcarbodiimide (15.7 mmol) were dissolved in 26.2 ml of dry tetrahydrofuran and stirred at room temperature for 10 min. Then, 1.81 (15.7 mmol) of N-hydroxysuccinimide in 14.1 ml of the same solvent were added and the reaction mixture was stirred at room temperature for 22.5 h. TLC analysis [CHCl₃/MeOH (50:1, v/v)] revealed a complete conversion of the educt. After this, the reaction mixture was filtrated by suction. The solvent was removed under reduced pressure and the residue was recrystallized from ethanol containing a trace of H₂O (34). The product was obtained as a colorless solid (3.08 g, 72%)

References:

Gantner, Martin;Schwarzmann, Günter;Sandhoff, Konrad;Kolter, Thomas [Journal of Lipid Research,2014,vol. 55,# 12,p. 2692 - 2704]