化学合成,医药中间体;生命科学。
氨酸甲酯盐酸盐属于氨基酸类衍生物,其可用作氨基酸合成的起始原料,也可用于制备各种含有氨基酸单元的生物活性分子,如多肽、蛋白质等。
合成路线 1(1. 合成:2491-20-5)
产率:100%
合成条件:Stage #1: at -15 - 0℃; Stage #2: for 3 h; Reflux
实验步骤:根据文献,L-丙氨酸用作底物以产生(S) - 丙氨酸甲酯盐酸盐(1a)。 (Xing et al。,2012)。向圆底烧瓶中加入15mL无水甲醇。在-15℃下将2.16mL SOCl 2(0.03mol)缓慢滴加到无水甲醇中并在0℃下保持1小时。用上述步骤将14mL无水甲醇和1.4mL(0.019mol)SOCl2加入另一个圆底烧瓶中。然后,将1.118g L-丙氨酸加入该溶液中并加热回流1.5小时。在减压下浓缩溶液后,将初始制备的SOCl 2溶液倒入圆底烧瓶中并继续回流1.5小时,得到1a(产率100%)。由于在该步骤中产生的盐酸不利于下一步反应,因此当回流结束时将NaHCO 3加入圆底烧瓶中以破坏其酸性,直至不再产生气泡。最后,将溶液浓缩,得到1b(产率100%)。将镰刀菌酸(4)和1b与15mL二氯甲烷一起放入圆底烧瓶中并均匀搅拌,然后加入过量的催化剂二环己基碳二亚胺(DCC)和4-加入二甲基氨基吡啶(DMAP)并回流24小时。在减压下浓缩溶液,并通过使用制备型HPLC(25-45%CH 3 CN / H 2 O,20分钟)纯化产物,得到1c(产率52%)。
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