N-(3-(2-呋喃基)丙烯酰基)苯丙氨酸的合成  

SYNTHESIS OF N-(3-(2-FURYL)ACRYLOYL)PHENYLALANINE

作　　者：黄朋勉[1] 陈金星 熊前政 郑晓斌 周智慧[1] 王梓鉴 吕彦博 周胜 Huang Pengmian;Chen Jinxing;Xiong Qianzheng;Zheng Xiaobin;Zhou Zhihui;Wang Zijian;Lv Yanbo;Zhou Sheng(School of Chemistry and Bioengineering,Changsha University of Science and Technology,Changsha 410114,Hu'nan,China;Hu'nan Spark Science Co.,Ltd.,Changsha 410114,Hu'nan,China;Lianyungang Duxiang Chemicals Co.,Ltd,Lianyungang 223500,Jiangsu,China)

机构地区：[1]长沙理工大学化学与生物工程学院,湖南长沙410114 [2]湖南斯派克科技股份有限公司,湖南长沙410000 [3]连云港笃翔化工有限公司,江苏连云港223500

出　　处：《精细石油化工》2018年第6期41-45,共5页Speciality Petrochemicals

基　　金：长沙市科技计划项目KQ1801052和KQ1801163

摘　　要：针对FAPGG关键体N-(3-(2-呋喃基)丙烯酰基)苯丙氨酸(FA-PHE-OH)收率和纯度低的问题,设计以糠醛和丙二酸为起始原料,经过Knoevenagel、甲酯化、酰基化及水解反应新路线制备FA-PHE-OH。得到的最佳制备工艺条件如下,2-呋喃丙烯酸为:反应温度95℃、反应时间5h、n(糠醛)∶n(丙二酸)=1∶1.2;3-(2-呋喃基)丙烯酰基-L-苯丙氨酸甲酯为:反应温度35℃、反应时间4h、n(2-呋喃丙烯酸)∶n(L-苯丙氨酸甲酯盐酸盐)=1∶1.2,本反应以SOCl_2代替BOP,收率提高76.6%,且成本大幅降低。在此条件下得到白色FA-PHE-OH产品,HPLC纯度99.5%,总收率80.2%。Aiming at low yield and purity of N-(3-(2-furyl)acryloyl)Phenylalanine(FA-PHE-OH)the key intermediate of N-[3-(2-furylacryloyl)]-L-phenyalanyl-glycyl-glycine (FAPGG),a new method was designed to synthesize it by knoevenagel,methylation,acylation and hydrolysis reaction using furfural and malonic acid as starting materials.The optimum conditions for the synthesis of 2-furana- crylic acid and 3-(2-furyl)acryloyl-L-phenylal-anine methyl ester were those as follows:reaction tem- perature of 95℃,reaction time of 5h,n(furfural):n(malonic acid)=1.2;reaction temperature of 35℃,reaction time of 5h,n(2-furan acrylic acid):n(L-phenylalanine methyl ester hydrochloride)= 1.2.The BOP was replaced with SOCl2in the acylation reaction with yield 76.6M increased and the cost greatly reduced.Under these conditions,the products were obtained as white solid with purity 99.5% (HPLC)and yield 80.2%.

关 键 词：N-(3-(2-呋喃基)丙烯酰基)苯丙氨酸 N-E3-(2-呋喃基)丙烯酰]-L苯丙氨酰-甘氨酰-甘氨酸 Kno-evenagel反应 酰基化反应 

分 类 号：TQ246.37[化学工程—有机化工]