酯型前药1-乙酰氧基乙基7-[(Z)-2-(2-氨基噻唑-4-基)-2-羟基亚氨基乙酰胺基]-3-[(Z)-1-丙烯基]-3-头孢烯-4-羧酸酯（BMY-28271）的合成改进
Improved synthesis of an ester-type prodrug, 1-acetoxyethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3-[(Z)-1- propenyl]-3-cephem-4-carboxylate (BMY-28271).
作者信息
Kamachi H, Okita T, Okuyama S, Hoshi H, Naito T
机构信息
Bristol-Myers Squibb Research Institute, Tokyo, Japan.
出版信息
J Antibiot (Tokyo). 1990 Dec;43(12):1564-72. doi: 10.7164/antibiotics.43.1564.
1-Acetoxyethyl 7-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3- [(Z)-1-propenyl]-3-cephem-4-carboxylate (BMY-28271) is an ester-type prodrug of cephalosporin for oral use. Methods suitable for large scale preparation were investigated. The yield was improved by esterification of 7-[(Z)-2-(2-aminothiazol-4-yl)-2-trityloxyiminoacetamido]cep hem-4-carboxylic acid (11) followed by removal of the trityl group and, in addition, column chromatographic purification at each step was eliminated by optimization of the reaction conditions.
7-[(Z)-2-(2-氨基噻唑-4-基)-2-羟基亚氨基乙酰胺基]-3-[(Z)-1-丙烯基]-3-头孢烯-4-羧酸1-乙酰氧基乙酯（BMY-28271）是一种用于口服的头孢菌素酯型前药。研究了适合大规模制备的方法。通过对7-[(Z)-2-(2-氨基噻唑-4-基)-2-三苯甲氧基亚氨基乙酰胺基]头孢烯-4-羧酸（11）进行酯化，然后除去三苯甲基，提高了产率，此外，通过优化反应条件，省去了每一步的柱色谱纯化。
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