Cefuroxime, Zinacef
头孢呋肟Chemical Name: [6R-[6alpha,7beta(Z)]]-3-[(Aminocarbonyl)oxy]ethyl]-7-[2-furanyl(methoxyimino)acetamido]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid
CAS No. 55268-75-2
项目整合开发状态: Launched-1977
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Compound can be prepared by several related ways:1) The reaction of diphenylmethyl (6R,7R)-3-hydroxymethyl-7-(2-thienylacetamido)ceph-3-em-4-carboxylate (I) with trichloroacetyl isocyanate (A) in anhydrous acetone gives the corresponding N-trichloroacetylcarbamate (II),which by reaction with PCl5 and pyridine in CH2Cl2 and then with p-toluenesulfonic acid affords diphenylmethyl 7-amino-3-carbamoyloxymethylceph-3-em-4-carboxylate p-toluenesulfonic acid salt (III).The hydrolysis of (III) with trifluoroacetic acid in anisole yields the corresponding acid (IV),which is finally condensed with 2-(2-furyl)-2-methoxyiminoacetic acid (V) by means of PCl5 and N,N-dimethylacetamide in acetonitrile containing triethylamine.2) The elimination of the protecting groups of compound (II) can also be performed stepwise with isolation of the intermediate p-toluenesulfonic salt (VI).3) The deprotected compound (III) can also be treated first with NaHCO3 and then condensed with the acetic acid (V) by means of dicyclohexylcarbodiimide in CH2Cl2 to give the diphenvimethyl ester (VII),which is finally hydrolyzed with trifluoroacetic acid.
📌 参考资料/链接：
参考文献标题:7-Hydrocarbonoxyiminoacetamido-3-carbamoyloxy methylceph-3-em-4 carboxylic acids
文献作者:Cook,M.C.; et al.(Glaxo Group Ltd.)
参考来源:US 3974153
📄 详细内容
合成路线:Compound can be prepared by several related ways:1) The reaction of diphenylmethyl (6R,7R)-3-hydroxymethyl-7-(2-thienylacetamido)ceph-3-em-4-carboxylate (I) with trichloroacetyl isocyanate (A) in anhydrous acetone gives the corresponding N-trichloroacetylcarbamate (II),which by reaction with PCl5 and pyridine in CH2Cl2 and then with p-toluenesulfonic acid affords diphenylmethyl 7-amino-3-carbamoyloxymethylceph-3-em-4-carboxylate p-toluenesulfonic acid salt (III).The hydrolysis of (III) with trifluoroacetic acid in anisole yields the corresponding acid (IV),which is finally condensed with 2-(2-furyl)-2-methoxyiminoacetic acid (V) by means of PCl5 and N,N-dimethylacetamide in acetonitrile containing triethylamine.2) The elimination of the protecting groups of compound (II) can also be performed stepwise with isolation of the intermediate p-toluenesulfonic salt (VI).3) The deprotected compound (III) can also be treated first with NaHCO3 and then condensed with the acetic acid (V) by means of dicyclohexylcarbodiimide in CH2Cl2 to give the diphenvimethyl ester (VII),which is finally hydrolyzed with trifluoroacetic acid.
参考文献标题:Cefuroxime
文献作者:Loren,J.G.; Castar,J.
参考来源:Drugs Fut 1978,3(4),266
产品链接: CAS No. 55268-75-2››