Analytical Chemistry and Spectroscopy
Wiley InterScience Backfile Collection 1832-2000
Chemistry and Pharmacology
The methoxime derivatives of N-acyl prostaglandin E2 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 PGE2 carboxamide was converted to the MO-TMS derivative of 9-keto-11,15-dihydroxy-prost-5,13-dienonitrile and the MO-TMS derivative of PGE2. 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.
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