REARRANGEMENT OF N-ACYL PROSTAGLANDIN CARBOXAMIDES TO NITRILES AND TRIMETHYLSILYL ESTERS

被引：1

作者：

FALKNER, FC

机构：

[1] Drug Metabolism Department, Pfizer Inc, Groton, Connecticut

来源：

BIOMEDICAL MASS SPECTROMETRY | 1979年 / 6卷 / 05期

关键词：

D O I：

10.1002/bms.1200060510

中图分类号：

R318 [生物医学工程];

学科分类号：

0831 ;

摘要：

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. Copyright © 1979 Heyden & Son Ltd

引用

页码：221 / 224

页数：4

共 10 条

[1]

CAMPAGNA F, 1977, TETRAHEDRON LETT, P1813

[2]

Challis B.C., 1970, CHEM AMIDES, P731

[3] NITRILE SYNTHESIS - DEHYDRATION OF AMIDES BY SILAZANES, CHLOROSILANES, ALKOXYSILANES, AND AMINOSILANES [J].