摘要
首次报道了声敏剂DEG的合成工艺。氯化血红素(2)在溴化氢的乙酸溶液中经脱铁及加成反应后,再与二乙二醇在浓硫酸催化下经醚化及酯化得7,12-双[1-[2-(羟基乙氧基)乙氧基]乙基]-3,8,13,17-四甲基卟啉-2,18-二丙酸二(2-羟基乙氧基)乙酯,收率83.2%。与无水乙醇经酯交换反应得7,12-双[1-[2-(羟基乙氧基)乙氧基]乙基]-3,8,13,17-四甲基卟啉-2,18-二丙酸二乙酯。然后按照先配位再水解的思路,先与四水合二氯化锰配位得锰-7,12-双[1-[2-(羟基乙氧基)乙氧基]乙基]-3,8,13,17-四甲基卟啉-2,18-二丙酸二乙酯,最后经氢氧化钠水解、盐酸酸化得目标化合物,纯度95.2%,总收率73.1%(以2计)。
The synthetic process of sonosensitizer DEG was reported in the first time. Hemin (2) was subjected to an addition and demetalation with hydrogen bromide in acetic acid, which was followed by an etherification and esterification with diethylene glycol under the catalysis of concentrated sulfuric acid to obtain di (2-hydroxyethoxy)- ethyl 7,12-bis [ 1 -[2-(hydroxyethoxy) ethoxy] ethyl]-3,8,13,17-tetramethyl porphyrin-2,18-dipropionate in 83.2% yield. Then it reacted with anhydrous ethanol via transesterification to give diethyl 7,12-(hydroxyethoxy)ethoxy]- ethyl]-3,8,13,17-tetramethyl porphyrin-2,18-dipropionate. The latter reacted with manganese dichloride tetrahydrate via coordination to afford diethyl manganese-7,12-bis[ 1 -[2-(hydroxyethoxy) ethoxy]ethyl]-3,8,13,17-tetramethyl porphyrin-2,18- dipropionate. Then after a hydrolysis with sodium hydroxide and an acidification with hydrochloric acid, the target compound DEG was obtained with a purity of 95.2% and an overall yield of 73.1 %(based on 2).
作者
陈俊磊
赵明
时志春
李军
张树军
CHEN Junlei;ZHAO Ming;SHI Zhichun;LI Jun;ZHANG Shujun(School of Chemistry and Chemistry Engineering, Qiqihar University, Qiqihar 161006)
出处
《中国医药工业杂志》
CAS
CSCD
北大核心
2019年第4期399-402,共4页
Chinese Journal of Pharmaceuticals
基金
黑龙江省省属高等学校基本科研业务费科研项目(YSTSXK201808)
齐齐哈尔大学研究生科技与创新项目(YJSCX2017-ZD10)
