Cefotaxime sodium, HR-756, Claforan
头孢噻肟钠 头孢噻肟 Chemical Name: (6R,7R)-3-(Acetoxymethyl)-7-[2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid sodium salt
CAS No. 64485-93-4, 63527-52-6 (free base)
项目整合开发状态: Launched-1980
项目研究机构: Aventis Pharma (Originator), Abbott (Licensee)
合成路线:The protection of the amino group of ethyl 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate (I) with trityl chloride (B) by means of triethylamine in CH2Cl2 gives ethyl 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino acetate (II),which is hydrolyzed to the corresponding acid (III) with NaOH in refluxing dioxane-water.The condensation of (III) with 7-aminocephalosporanic acid (IV) by means of dicyclohexylcarbodiimide in CH2Cl2 containing triethylamine affords 7-(2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]cephalosporanic acid (V).The elimination of the trityl group is performed with hot 55% formic acid yielding the corresponding free acid,which is finally treated with NaHCO3 in water.
📌 参考资料/链接：
参考文献标题:Oxime derivatives of 7-aminothiazolylacetamidocephalosporanic acid processes for preparing them and pharmaceutical compositions incorporating them
文献作者:Heymes,R.; Lutz,A.(Aventis Pharma SA)
参考来源:BE 0850662; ES 455089; ES 466539; GB 1580621; GB 1580623; JP 52102293; JP 5247013
📄 详细内容
合成路线:The protection of the amino group of ethyl 2-(2-amino-4-thiazolyl)-2-methoxyiminoacetate (I) with trityl chloride (B) by means of triethylamine in CH2Cl2 gives ethyl 2-(2-tritylamino-4-thiazolyl)-2-methoxyimino acetate (II),which is hydrolyzed to the corresponding acid (III) with NaOH in refluxing dioxane-water.The condensation of (III) with 7-aminocephalosporanic acid (IV) by means of dicyclohexylcarbodiimide in CH2Cl2 containing triethylamine affords 7-(2-(2-tritylamino-4-thiazolyl)-2-methoxyiminoacetamido]cephalosporanic acid (V).The elimination of the trityl group is performed with hot 55% formic acid yielding the corresponding free acid,which is finally treated with NaHCO3 in water.
参考文献标题:HR-756
文献作者:Castar,J.; Neuman,M.
参考来源:Drugs Fut 1978,3(10),749
产品链接: CAS No. 64485-93-4›› 产品链接: CAS No.63527-52-6››