侧链带脲基的β-氨基酸的设计合成

Design and synthesis of β-amino acids bearing an ureido group in their side chains

以廉价的L-天冬氨酸为原料,成功设计合成了3个侧链带脲基的Boc保护的新的β-氨基酸。在分别对L-天冬氨酸的β-位羧基和氨基保护后,将其α-位羧基转化为酰基叠氮,该酰基叠氮经Curtius重排,成功得到合成脲的重要中间体异氰酸酯。所选取的胺都能与异氰酸酯迅速作用,得到期望的目标化合物,这些目标化合物结构经核磁氢谱、质谱确证。

Using commercial L-aspartic acid as the starting material, three new Boc-protected β-amino acids bearing an ureido group in their side chains were designed and prepared. After the β-carboxyl and amino groups of L-aspartic acid were protected, the α-carboxyl radical of compound 2 was converted to acyl azide. The important intermediate isocyanate was obtained successfully by a Curtius rearrangement of acyl azide. Upon quick reaction of isocyanate with amines, the desired β-amino acids bearing an ureido group in their side chains were readily obtained. The target compounds were characterized by ^1HNMR and MS spectra.