Tan Chengxia
2010
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Journal
Journal of Chemical Engineering of Chinese Universities
Abstract
1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)-1H-1,2,4-triazole-3-carboxylic acid methyl ester, which is called "derivative of Ribavirin" for short, is an important intermediate of Ribavirin which is a broad-spectrum antiviral drug. In this study, the derivative of Ribavirin was synthesized with the reaction of using 1,2,4-triazole-3-carboxylic acid methyl ester and 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose as raw materials and solid superacid SO42-/TiO2 as catalyst. Various factors affecting the synthesis reaction were investigated, and the reaction conditions were optimized. The results show that the suitable synthesis conditions are as follows: the amount of catalyst SO42-/TiO2 used is 12%(mass) of the tetra-acetyl-D-ribofuranose used, the mole ratio of 1,2,3,5-tetra-O-acetyl-β-D-ribofuranose to 1,2,4-triazole-3-carboxylic acid methyl ester is 1:1.05, the reaction temperature is 100~110℃ and the reaction time is 2 h. Using the above optimized conditions, the yield of the product is 87.0% and its purity is 99.5%. The proposed synthetic route for synthesizing derivative of Ribavirin has following advantages: the preparation of the catalyst SO42-/TiO2 is simple, the catalyst has higher catalytic efficiency and can easily be removed from the product and be regenerated and reused cyclically, the synthesis process is environmentally benign and its operation is simple, both the color and purity of the product are good.