期刊论文详细信息
Beilstein Journal of Organic Chemistry
Preparation of mixed trialkyl alkylcarbonate derivatives of etidronic acid via an unusual route
Petri A. Turhanen1  Janne Weisell1  Jouko J. Vepsäläinen1 
[1] University of Eastern Finland, School of Pharmacy, Biocenter Kuopio, P.O. Box 1627, FIN-70211, Kuopio, Finland;
关键词: alkyl carbonate;    bisphosphonate;    etidronate;    ester;    synthesis;   
DOI  :  10.3762/bjoc.8.228
来源: DOAJ
【 摘 要 】

A method to prepare four (3a–d) trialkyl alkylcarbonate esters of etidronate from P,P'-dimethyl etidronate and alkyl chloroformate was developed by utilizing unexpected demethylation and decarboxylation reactions. The reaction with the sterically more hindered isobutyl chloroformate at a lower temperature (90 °C) produced the P,P'-diester (2) as a stable intermediate product. A possible reaction mechanism is discussed to explain these methyl substitutions. These unusual reactions also clarify why it is difficult to prepare alkylcarbonate prodrugs from bisphosphonates. The compounds prepared were analysed by spectroscopic techniques.

【 授权许可】

Unknown   

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