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【结 构 式】

【药物名称】Cefteram, T-2525

【化学名称】[6R-[6alpha,7beta(Z)]]-7-[2-(2-Aminothiazol-4-yl)-2-(methoxyimino)acetamido]-3-(5-methyl-2H-tetrazol-2-ylmethyl)-3-cephem-4-carboxylic acid

【CA登记号】82547-58-8

【 分 子 式 】C16H17N9O5S2

【 分 子 量 】479.49919

【开发单位】Toyama (Originator)

【药理作用】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 diphenyldiazomethane (IV) as usual to the ester (V). The condensation of (V) with 2-(tert-amyloxycarboxamidothiazol-4-yl)- 2-(methoxyimino)acetic acid (VI) by means of ethyl chlorocarbonate and N-methylmorpholine in CH2Cl2 affords the fully protected compound (VII), which is finally deprotected with trifluoroacetic acid.

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) 24728 2-diazopropane C3H6N2 详情 详情
(V) 24729 benzyl 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 C17H18N6O3S 详情 详情
(VI) 24730 2-[2-[(hexanoyloxy)amino]-1,3-thiazol-4-yl]-2-(methoxyimino)acetic acid C12H17N3O5S 详情 详情
(VII) 24731 benzhydryl 7-[[2-[2-[(hexanoyloxy)amino]-1,3-thiazol-4-yl]-2-(methoxyimino)acetyl]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 C35H37N9O7S2 详情 详情
Extended Information