The N-Fmoc-O-acetyl-L-tyrosine(compound 3) was achieved from materials of L-tyrosine,N-(9-Fluorenylmethoxycarbonyloxy)succinimide and acetic anhydride via Fmoc-amino protection,acetylation of phenolic hydroxyl.The target compound of N′-adamantyl-N-Fmoc-O-acetyl-L-tyramine(compound 1) was synthesized from condensation by intermediate and amantadine under 1-(3-dimethylamino propyl)-3-ethyl carbodiimide hydrochloride as(EDC.HCl) condensing agent and methylene chloride as solvent.The total yield was 18.75 %.The fragmentation mechanism of compound was obtained by fragment peaks of MS/MS spectrum,which provides the basis information of MS spectrum for confirming its structure.Reaction conditions were optimized,and the appropriate protectants as well as catalysts were finally defined.%以L-酪氨酸、9-芴甲基-N-琥珀酰亚胺基碳酸酯和乙酸酐为原料,经过Fmoc氨基保护,酚羟基乙酰化,制得中间体N-Fmoc-O-乙酰基-L-酪氨酸(化合物3);在1-(3-二甲氨基丙基)-3-乙基碳二亚胺盐酸盐(EDC.HCl)为缩合剂、二氯甲烷为溶剂的条件下,与金刚烷胺缩合,合成了目标化合物N'-金刚烷基-N-Fmoc-O-乙酰基-L-酪氨酰胺(化合物1),3步总收率为18.75%.根据二级质谱碎片峰,给出化合物的裂解途径,为其结构确证提供质谱依据.实验过程中,对各步反应条件进行优化,并最终确定合适的保护剂和催化剂.
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