Premium
Rearrangement of N‐ acyl prostaglandin carboxamides to nitriles and trimethylsilyl esters
Author(s) -
Falkner Fred C.
Publication year - 1979
Publication title -
biomedical mass spectrometry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.475
H-Index - 121
eISSN - 1096-9888
pISSN - 0306-042X
DOI - 10.1002/bms.1200060510
Subject(s) - trimethylsilyl , chemistry , moiety , derivative (finance) , silylation , imide , prostaglandin , medicinal chemistry , carboxamide , stereochemistry , organic chemistry , biochemistry , catalysis , financial economics , economics
The methoxime derivatives of N ‐acyl prostaglandin E 2 carboxamides (PG imides), when analyzed in the presence of excess N,O ‐bis(trimethylsilyl)trifluoroacetamide by gas chromatography, were converted to nitriles and trimethylsilyl esters. For example, the methoximetrimethylsilyl (MO‐TMS) derivative of N ‐acetyl PGE 2 carboxamide was converted to the MO‐TMS derivative of 9‐keto‐11,15‐dihydroxy‐prost‐5,13‐dienonitrile and the MO‐TMS derivative of PGE 2 . The ratio of rearrangement products was found to be dependent upon the nature of the N ‐acyl group, and the rearrangement apparently took place in the vapor phase after silylation of the imide moiety.