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Synthesis of 7-Arylidene Cephalosporanates for ${\beta}-lactamase$ Inhibitor  

Lee, Jong-Min (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University)
Yim, Chul-Bu (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University)
Im, Chae-Uk (Division of Medicinal Chemistry, College of Pharmacy, Chung-ang University)
Publication Information
YAKHAK HOEJI / v.52, no.4, 2008 , pp. 311-315 More about this Journal
Abstract
The synthesis of 7-arylidene cephalosporanates for ${\beta}-lactamase$ inhibitor was described. The reactions of substituted benzyl halides $[1]{\sim}[3]$ with triphenylphosphine gave triphenylphcsphonium chlorides $[4]{\sim}[6]$. These phosphonium salts were treated with n-butyllithium to give ylides, which were reated with 7-oxocephalosporanate [7] by Wittig reaction to afford the 7-exomethylene cephalosporanates $[8]{\sim}[10]$. These cephalosporanates were oxidized to cephalosporanate sulfones $[11]{\sim}[13]$ with mCPBA. The deprotection of benzhydryl cephalosporanate $[8]{\sim}[13]$ with $AlCl_3$ and $NaHCO_{3}$ gave sodium salts of 7-arylidene cephalosporanates $[14]{\sim}[19]$.
Keywords
7-arylidene cephalosporanates${\beta}-lactamase$ inhibitors;
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