|
【结 构 式】 
|
【药物名称】Cefuroxime axetil, SN-407, CCI-15641, Lifurox, Zinat, Elobact, Ceftin, Zinnat, Maxitil 【化学名称】[6R-[6alpha,7beta(Z)]]-3-[[(Aminocarbonyl)oxy]methyl]-7-[[2-furanyl(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid 1-(acetyloxy)ethyl ester 【CA登记号】64544-07-6, 55268-75-2 (free acid), 56238-63-2 (Na salt) 【 分 子 式 】C20H22N4O10S 【 分 子 量 】510.48314 |
【开发单位】GlaxoSmithKline (Originator) 【药理作用】Antibiotics, ANTIINFECTIVE THERAPY, Cephalosporins |
合成路线1
The reaction of 3-hydroxymethyl-7-[2-(2-furyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (I) with chlorosulfonyl isocyanate (II) and then with sodium 2-ethylhexanoate gives sodium cefuroxime (III), which is then treated with 1-bromoethyl acetate (IV) in DMA.
| 【1】 Gregson, M.; Sykes, R.B. (Glaxo Group Ltd.); Cephalosporins antibiotics. DE 2706413; FR 2340950; JP 52100494; US 4267320 . |
| 【2】 Crisp, H.A.; Clayton, J.C. (Glaxo Group Ltd.); Amorphous form of cefuroxime ester. DE 3327449; EP 0107276; FR 2531087; GB 2127401; JP 59044391; US 4562181; US 4820833; US 4994567; US 55013833 . |
| 【3】 Serradell, M.N.; Castaner, J.; Cefuroxime Axetil. Drugs Fut 1985, 10, 2, 112. |
| 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) | 28972 | (6R,7R)-7-[[2-(2-furyl)-2-(methoxyimino)acetyl]amino]-3-(hydroxymethyl)-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid | C15H15N3O7S | 详情 | 详情 | |
| (II) | 29873 | (2R,3R,4S,5R)-5-(6-chloro-9H-purin-9-yl)-4-fluoro-2-[(trityloxy)methyl]tetrahydro-3-furanyl benzoate | C36H28ClFN4O4 | 详情 | 详情 | |
| (III) | 28974 | sodium (6R,7R)-3-[[(aminocarbonyl)oxy]methyl]-7-[[2-(2-furyl)-2-(methoxyimino)acetyl]amino]-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate | C16H15N4NaO8S | 详情 | 详情 | |
| (IV) | 12282 | 1-bromoethyl acetate | C4H7BrO2 | 详情 | 详情 |
Extended Information