Preparation and characterization of methyl 11‐amino‐(N‐p‐toluenesulfonyl)‐9‐E‐octadecenoate and methyl 8‐amino‐(N‐p‐toluenesulfonyl)‐9‐E‐octadecenoate

Abstract

Allylic amination of methyl oleate with bis(N-ptoluenesulfonyl) sulfodiimide results in a mixture of methyl 11amino-(N-p-toluenesulfonyl)-9-E-octadecenoate and methyl 8amino-(N-p-toluenesulfonyl)-9-E-octadecenoate in 58% yield. These novel products were isolated and characterized by nuclear magnetic resonance, infrared spectroscopy, mass spectrometry, and melting point. The reaction was analyzed by highperformance liquid chromatography and thin-layer chromatography. JAOCS 73, 229-234 (1997).

Fatty acids, fatty acid analogues and their derivatives

“…261 Allylic amination of methyl oleate with bis(N-p-toluenesulfonyl)sulfodiimide gave a mixture of methyl 11-amino-(N-p-toluenesulfonyl)-18:1(9E) and methyl 8-amino-(N-p-toluenesulfonyl)-18:1(9E). 262 Thermal reactions of fatty acids with diethylene triamine gave 1,3-diamides in vacuo, but when carried out in a solvent (xylene) 1,2-diamide was produced which formed imidazolines. 263 The dehydration reaction kinetics of castor oil [with 12-hydroxy-18:1(9Z) as the major component] was investigated with sodium bisulfate-sodium bisulfite mixture or toluene-p-sulfonic acid as catalyst.…”