Synthesis
Myristic acid (3.00 g, 13.1 mmol) and N,N'-dicyclohexylcarbodiimide (3.24 g, 15.7 mmol) were dissolved in 26.2 mL of anhydrous tetrahydrofuran and stirred at room temperature for 10 minutes. Subsequently, a solution of N-hydroxysuccinimide (1.81 g, 15.7 mmol) dissolved in 14.1 mL of the same solvent was added and the reaction mixture continued to be stirred for 22.5 h at room temperature. Complete conversion of the feedstock was confirmed by thin layer chromatographic analysis [CHCl3/MeOH (50:1, v/v)]. Upon completion of the reaction, insoluble material was removed by diafiltration. The solvent was removed by concentration under reduced pressure and the residue was recrystallized from ethanol containing traces of water to afford the target product 2,5-dioxopyrrolidin-1-yl tetradecanoate as a colorless solid (3.08 g, 72% yield). The product was characterized by 1H-NMR (300 MHz, CDCl3), 13C-NMR (75 MHz, CDCl3), EI-MS and elemental analysis (CHN), and the data were consistent with the expected structure.
References
[1] RSC Advances, 2015, vol. 5, # 81, p. 66339 - 66354
[2] Journal of Pharmaceutical Sciences, 1994, vol. 83, # 2, p. 233 - 238
[3] Journal of Pharmacology and Experimental Therapeutics, 2004, vol. 309, # 1, p. 340 - 347
[4] Angewandte Chemie, 1996, vol. 108, # 15, p. 1791 - 1794
[5] Journal of Mass Spectrometry, 1995, vol. 30, # 6, p. 900 - 910
