| 第 35 卷第 6 期 |  | Vol. 35 No. 6 | | 2005 年 12 月 | Dec 2005 |
|
所屬欄目：醫藥及中間體
(2,6-二氯-5-氟-吡啶-3-羰基)-乙酸乙酯的合成 |
| 陳磊; 高忠良; 劉雁; 朱秋峰(河北工業(yè)大學(xué)應用化學(xué)系) |
| 摘 要：(2,6-二氯-5-氟-吡啶-3-羰基)-乙酸乙酯是合成沙星類(lèi)藥物和其他喹諾酮類(lèi)抗菌藥的關(guān)鍵中間體。以2,6-二氯-5-氟-吡啶-3-羧酸,二氯亞砜為原料發(fā)生親核取代反應制得2,6-二氯-5-氟-吡啶-3-酰氯;以β二羰基化合物丙二酸二乙酯與乙醇鎂反應生成強親核試劑[C2H(COOC2H5)2]-碳負離子;它再與2,6-二氯-5-氟-吡啶-3-酰氯發(fā)生親核取代反應制得(2,6-二氯-5-氟-吡啶-3-羰基)丙二酸乙酸乙酯;在對甲苯磺酸的作用下經(jīng)過(guò)酯的水解和β-二酸的脫羧得目的產(chǎn)物(2,6-二氯-5-氟-吡啶-3-羰基)-乙酸乙酯。對反應條件進(jìn)行了改進(jìn),選用了比較廉價(jià)的原料,并對重結晶試劑進(jìn)行了深入的篩選,得到具有良好晶形的目的產(chǎn)物。 |
| 關(guān)鍵詞：喹諾酮; （2; 6-二氯-5-氟-吡啶-3-羰基）-乙酸乙酯; 結晶; 碳負離子 |
| 中圖分類(lèi)號：TQ253.21 文獻標識碼：A 文章編號：1009-9212(2005)06-0029-03 |
|
| Synthesis of ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propionate |
| CHEN Lei; GAO Zhong-liang; LIU Yan; ZHU Qiu-feng（School of Chemical Engineering; Hebei University of Technology; Tianjin 300130; China） |
| Abstract：Ethyl 3-(2,6-dichloro-5-fluoropyridin-3-yl)-3-oxo-propionate is the key of the synthesis of Quinolone antibacterial agents.2,6-dichloro-5-fluoro-nicotine acid was treated with Sulphurous oxychloride,to give 2,6-dichloro-5-fluoronicotinoyl chloride,then reacted to carbanion.The resultant was treated with p-Toluenesulfonic acid,to give the resultant we need.We improve on the reaction,using the cheap material,and selected the best one of the reagent to give the best of the resultant with nicer crystal. |
| Key words：quinolone; ethyl 3-（2; 6-dichloro-5-fluoropyridin-3-yl）-3-oxo-propionate; crystal carbanion |
|
收稿日期：2005-08-27
|
| 閱讀全文 |
|