|
【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 |