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PREPARATION OF 4-AMINO-5-HEXENOIC ACID

机译:4-氨基-5-己酸的制备

摘要

PURPOSE: A new preparation of 4-amino-5-hexenoic acid is provided that produces economically 4-amino-5-hexenoic acid through simple processes using glutamic acid-5-benzylester as a starting material. CONSTITUTION: The preparation of 4-amino-5-hexenoic acid (vinyl γ-aminobutyric acid) comprises the step of preparing the desired compound via new intermediates of Formula (II), (III) and (IV) from glutamic acid-5-benzylester of Formula (I) derived from glutamic acid. More particularly, the preparation of 4-amino-5-hexenoic acid of Formula (A) comprises hydrolyzing 4-£(benzyloxy)carbonyl|amino-5-hexenoic acid benzyl ester £Formula (IV)| in the presence of Pd/C catalyst. The preparation of the desired compound (I) comprises the step of subjecting benzyl-4-{£(benzyloxy)carbonyl|amino}-5-oxopentanoate £Formula (III)| to a Wittig reaction. Also, the preparation of benzyl-4-{£(benzyloxy)carbonyl|amino}-5-oxopentanoate £Formula (III)| comprises the steps of reacting glutamic acid-5-benzylester £Formula (I)| with benzyl chloroformate to provide N-benzyloxycarbonyl glutamic acid-5-benzylester £Formula (II)|, and then directly reducing the compound of Formula (II) or converting the carboxyl group of the compound represented by Formula (II) to an alcohol group using NaBH4 and ethylchloroformate followed by subjecting to a Swern Oxidation.
机译:目的:提供了一种新的4-氨基-5-己酸的制备方法,该方法以谷氨酸-5-苄基酯为起始原料,通过简单的方法经济地生产了4-氨基-5-己酸。组成:4-氨基-5-己酸(乙烯基γ-氨基丁酸)的制备包括通过谷氨酸-5经由式(II),(III)和(IV)的新中间体制备所需化合物的步骤。衍生自谷氨酸的式(I)的-苄基酯。更特别地,式(A)的4-氨基-5-己酸的制备包括水解4-((苄氧基)羰基|氨基-5-己酸苄酯)式(IV)|。在Pd / C催化剂存在下。所需化合物(I)的制备包括以下步骤:使-4- {oxy(苄氧基)羰基|氨基} -5-氧戊酸苄酯£维蒂希反应。另外,制备4- {£(苄氧基)羰基|氨基} -5-氧戊酸苄酯£通式(III)|的制备。包括使谷氨酸5-苄基酯反应的步骤用氯甲酸苄酯提供N-苄氧基羰基谷氨酸-5-苄酯£式(II)|,然后直接还原式(II)的化合物或将式(II)表示的化合物的羧基转化为醇基使用NaBH4和氯甲酸乙酯,然后进行Swern氧化。

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