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Preparation and characterization of methyl 11‐amino‐( N‐p ‐toluenesulfonyl)‐9‐ E ‐octadecenoate and methyl 8‐amino‐( N‐p ‐toluenesulfonyl)‐9‐ E ‐octadecenoate
Author(s) -
Herron Barry F.,
Bagby Marvin O.,
Isbell Terry A.,
Byrdwell Wm. Craig,
Plattner Ron,
Weisleder David
Publication year - 1997
Publication title -
journal of the american oil chemists' society
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.512
H-Index - 117
eISSN - 1558-9331
pISSN - 0003-021X
DOI - 10.1007/s11746-997-0128-7
Subject(s) - chemistry , amination , allylic rearrangement , yield (engineering) , mass spectrometry , nuclear magnetic resonance spectroscopy , amino acid , melting point , medicinal chemistry , organic chemistry , chromatography , catalysis , biochemistry , materials science , metallurgy
Allylic amination of methyl oleate with bis( N‐p ‐toluenesulfonyl) sulfodiimide results in a mixture of methyl 11‐amino‐( N‐p ‐toluenesulfonyl)‐9‐ E ‐octadecenoate and methyl 8‐amino‐( 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.