Nicotinic Acid → HCID 53842741, compound

Participants

Reaction Steps

To a solution of 77 mg (0.63 mmol) of nicotinic acid in a mixed solvent of tetrahydrofuran (2 ml) and 1,2-dichloroethane (2 ml) at room temperature were successively added in an atmosphere of argon 7 mg (0.06 mmol) of 4-dimethylaminopyridine, 129 mg (0.63 mmol) of N,N'-dicyclohexylcarbodiimide and 196 mg (0.57 mmol) of N-5,8,11,14,17-eicosapentaenoyl-2-aminoethanol, which were dissolved in 1,2-dichloroethane (1.5 ml), respectively. The mixture was reacted overnight, and precipitates then produced were separated by filtration and washed with benzene. To the mother liquor was added water, and the mixture was extracted three times with dichloromethane. The organic layer from the extraction was washed with water and dried over anhydrous sodium sulfate. The solvent was then removed by distillation under reduced pressure to give 311 mg of extraction residue, which was subjected to silica gel column chromatography. From a fraction eluted with chloroform-methanol (98:2) was obtained 246 mg (0.55 mmol) of N-(5,8,11,14,17-eicosapentaenoyl)-2-aminoethyl nicotinate. Physicochemical properties of the product supports the formula (III) shown below.

Provenance & Evidence