CM-40874
Chemical Name: 7-[2-(2-Amino-4-thiazolyl)-2-[(2-carboxy-2-propoxy)imino]acetamido]-3-[[(1-allylpyridinium-2-yl)thio]methyl]-3-cephem-4-carboxylic acid 1-oxide bromide
项目整合开发状态: Biological Testing
项目研究机构: Sanofi-Synth閘abo (Originator)
合成路线:The condensation of 7-amino-3-bromomethyl-3-cephem-4-carboxylic acid tert-butyl ester 1-oxide (I) with 2-(2-tritylamino-4-thiazolyl)-2-[2-(tert-butoxycarbonyl)-2-propyloxyimino]acetic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives the corresponding amide (III),which is treated with N-allyl-pyridine-2-thione (IV) in dimethylacetamide yielding the pyridinium salt (V).Finally,this compound is deprotected by a treatment with HCl in formic acid.The thione (IV) is prepared as follows: The reaction of 2-bromopyridine (VI) with allyl bromide (VII) in acetone gives N-allyl-2-bromopyridinium bromide (VIII),which is then treated with potassium hydrosulfide in water.
📌 参考资料/链接：
参考文献标题:Derivatives of pyridinium thiomethyl cephalosporins
文献作者:Labeeuw,B.; Salhi,A.(Sanofi-Synthabo)
参考来源:EP 0088853; FR 2516515; JP 58090590; US 4593022
📄 详细内容
合成路线:The condensation of 7-amino-3-bromomethyl-3-cephem-4-carboxylic acid tert-butyl ester 1-oxide (I) with 2-(2-tritylamino-4-thiazolyl)-2-[2-(tert-butoxycarbonyl)-2-propyloxyimino]acetic acid (II) by means of dicyclohexylcarbodiimide in CH2Cl2 gives the corresponding amide (III),which is treated with N-allyl-pyridine-2-thione (IV) in dimethylacetamide yielding the pyridinium salt (V).Finally,this compound is deprotected by a treatment with HCl in formic acid.The thione (IV) is prepared as follows: The reaction of 2-bromopyridine (VI) with allyl bromide (VII) in acetone gives N-allyl-2-bromopyridinium bromide (VIII),which is then treated with potassium hydrosulfide in water.
参考文献标题:CM-40874
文献作者:Serradell,M.N.; Matthews,R.; Casta馿r,J.; Burnie,J.
参考来源:Drugs Fut 1985,10(3),193