Formidacillin, Fomidacillin sodium, BRL-36650
福米西林Chemical Name: 6beta-[D-2-[(4-Ethyl-2,3-dioxopiperazin-1-yl)carbonylamino]-2-(3,4-dihydroxyphenyl)acetamido]-6alpha-formamidopenicillinic acid sodium salt
CAS No. 98048-07-8 (free acid)
项目整合开发状态: Preclinical
项目研究机构: GlaxoSmithKline (Originator)
合成路线:The acylation of 3,4-dihydroxyphenylglycine (I) with 4-ethyl-2,3-dioxopiperazin-1-ylcarbonyl chloride (II) by means of N,N-diethyl-1,1,1-trimethylsilylamine (DTSA) gives the corresponding N-acyl derivative (III),which is acetylated with acetic anhydride and pyridine in THF yielding the corresponding diacetoxy compound (IV).The condensation of (IV) with benzyl 6B-amino-6a-formamidopenicillanate (V) [obtained from the trichloroethoxycarbonyl derivative (VI)] by means of dicyclohexyl carbodiimide (DCC) in dichloroethane affords the fully protected compound (VII),which is debenzylated by hydrogenolysis with H2 over Pd/C in THF - water giving the free acid (VIII).Finally,this compound is desacetylated with Subtilisin Calsberg.
📌 参考资料/链接：
参考文献标题:beta -Lactam antibacterial agents
文献作者:Milner,P.H.(SmithKline Beecham plc)
参考来源:EP 0071395; GB 2107307; US 4539149; US 4609652; US 4877783
📄 详细内容
合成路线:The acylation of 3,4-dihydroxyphenylglycine (I) with 4-ethyl-2,3-dioxopiperazin-1-ylcarbonyl chloride (II) by means of N,N-diethyl-1,1,1-trimethylsilylamine (DTSA) gives the corresponding N-acyl derivative (III),which is acetylated with acetic anhydride and pyridine in THF yielding the corresponding diacetoxy compound (IV).The condensation of (IV) with benzyl 6B-amino-6a-formamidopenicillanate (V) [obtained from the trichloroethoxycarbonyl derivative (VI)] by means of dicyclohexyl carbodiimide (DCC) in dichloroethane affords the fully protected compound (VII),which is debenzylated by hydrogenolysis with H2 over Pd/C in THF - water giving the free acid (VIII).Finally,this compound is desacetylated with Subtilisin Calsberg.
参考文献标题:Formidacillin sodium
文献作者:Prous,J.; Castar,J.
参考来源:Drugs Fut 1986,11(9),739
产品链接: CAS No. 98048-07-8››