β-Lactamase 억제작용이 기대되는 7-Arylidene Cephalosporanate 유도체의 합성

Synthesis of 7-Arylidene Cephalosporanates for β-Lactamase Inhibitor

The synthesis of 7-arylidene cephalosporanates for β-lactamase inhibitor was described. The reactions of substituted benzyl halides [1]~[3] with triphenylphosphine gave triphenylphosphonium chlorides [4]~[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]~[10]. These cephalosporanates were oxidized to cephalosporanate sulfones [11]~[13] with mCPBA. The deprotection of benzhydryl cephalosporanate [8]~[13] with AlCl3 and NaHCO3 gave sodium salts of 7-arylidene cephalosporanates [14]~[19].