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目的研究磷酸奥司米韦的合成方法。方法以莽草酸为起始原料,通过酯化、缩酮保护、甲磺酰化、缩酮交换、还原,闭环反应得关键中间体(3R,4S,5S)-4,5-环氧基-3-(1-乙基丙氧基)-1-环己烯甲酸乙酯(2);化合物2在氯化镁催化下和叔丁胺反应,经甲磺酰化、闭环得氮丙啶中间体,再经开环、乙酰化、脱叔丁基、脱烯丙基、成磷酸盐共13步反应得抗病毒药磷酸奥司米韦。结果与结论合成的磷酸奥司米韦经1H-NMR和M S谱确证结构,总收率为29.5%。
Objective To study the synthesis of oseltamivir phosphate. Methods Shikimic acid was used as the starting material to prepare the key intermediates (3R, 4S, 5S) -4,5-epoxy-phenylalanine by esterification, ketal protection, mesylation, ketal exchange, Ethyl 2-ethyl 3- (1-ethylpropyloxy) -1-cyclohexenecarboxylate; Compound 2 was reacted with t-butylamine under the catalysis of magnesium chloride and the aziridine intermediate was cyclized by mesylation to form Open-loop, acetylation, off tert-butyl, de-allyl, phosphate into a total of 13 steps to obtain antiviral drug oseltamivir. RESULTS AND CONCLUSIONS The synthesized oseltamivir phosphate was confirmed by 1H-NMR and MS spectra. The overall yield was 29.5%.