Cefteram pivoxil, Ro-19-5248, T-2588, Tomiron, -Drug Synthesis Database

【结构式】

【药物名称】Cefteram pivoxil, Ro-19-5248, T-2588, Tomiron

【化学名称】[6R-(6alpha,7beta)]-7-[2-(2-Amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid (2,2-dimethyl-1-oxopropoxy)methyl ester
　　　　　　(6R,7R)-7-[2-(2-Amino-4-thiazolyl)-2(Z)-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid pivaloyloxymethyl ester

【CA登记号】82547-81-7, 82556-89-6 (monoHCl)

【分子式】C₂₂H₂₇N₉O₇S₂

【分子量】593.64459

【开发单位】Toyama (Originator), Showa Sangyo (Comarketer)

【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, DENTAL AGENTS, Cephalosporins

合成路线1

The condensation of 7-aminocephalosporanic acid (I) with 5-methyltetrazole (II) by means of BF3 ethyl ether in sulfolane gives 7-amino-3-(5-methyl-1,2,3,4-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid (III), which is esterified with pivaloyloxymethyl iodide (IV) by means of triethylamine in DMF yielding the corresponding ester (V). Finally, this compound it condensed with 2-(2-aminothiazol-4-yl)-2-(methoxyimino)acetic acid (VI) by means of POCl3 and dimethylacetamide in CH2Cl2.

参考文献中间体

【1】 Hirakawa, T.; Imaizumi, H.; Inaba, T.; Konishi, Y.; Narita, H.; Sadaki, H.; Saikawa, I.; Tai, M.; Taki, H.; Watanabe, Y. (Toyama Chemical Co., Ltd.); Cephalosporins. AU 8549860; AU 8549863; DE 3137854; US 4489072 .
【2】 Serradell, M.N.; Castaner, J.; Cefteram. Drugs Fut 1986, 11, 9, 732.

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
(I)	15672	7-Aminocephalosporanic acid; 3-[(acetoxy)methyl]-7-amino-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid; 7-ACA		C₁₀H₁₂N₂O₅S	详情	详情
(II)	24726	5-methyl-2H-1,2,3,4-tetraazole	4076-36-2	C₂H₄N₄	详情	详情
(III)	24727	7-amino-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid		C₁₀H₁₂N₆O₃S	详情	详情
(IV)	24735	tert-Butyl 2-iodoacetate		C₆H₁₁IO₂	详情	详情
(V)	24736	[(2,2-dimethylpropanoyl)oxy]methyl 7-amino-3-[(5-methyl-2H-1,2,3,4-tetraazol-2-yl)methyl]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate		C₁₆H₂₂N₆O₅S	详情	详情
(VI)	24737	2-(2-amino-1,3-thiazol-4-yl)-2-(methoxyimino)acetic acid	65872-41-5	C₆H₇N₃O₃S	详情	详情

Extended Information