Pátek M, Smrcina M, Nakanishi E, Izawa H
Selectide Corporation, a subsidiary of Aventis Pharmaceutical Inc., 1580 East Hanley Boulevard, Tucson, Arizona 85737, USA.
J Comb Chem. 2000 Jul-Aug;2(4):370-7. doi: 10.1021/cc0000141.
A novel acid labile linker for solid-phase synthesis of substituted guanidines has been developed. Its synthetic utility is exemplified by high-yielding pyrazole displacement with structurally and electronically diverse sets of aliphatic and aromatic amines. The final cleavage is achieved by treatment with 95:5 trifluoroacetic acid/water for 1 h. The corresponding guanidines were obtained in high purity (80-95%) and good isolated yields (50-95%). The scope and limitations of this linker were further demonstrated by the solid-phase synthesis of an 880-member library of individual trisubstituted arylguanidines employing pyrazole displacement with a set of 11 anilines and two subsequent Mitsunobu N-alkylations with sets of 10 and 8 alcohols, respectively.
已开发出一种用于固相合成取代胍的新型酸不稳定连接基。通过用结构和电子性质多样的脂肪族和芳香族胺进行高产率的吡唑取代反应，例证了其合成效用。通过用95:5的三氟乙酸/水处理1小时实现最终裂解。以高纯度（80 - 95%）和良好的分离产率（50 - 95%）获得了相应的胍。通过使用11种苯胺进行吡唑取代反应以及随后分别使用10种和8种醇进行两组 Mitsunobu N - 烷基化反应，固相合成一个包含880个个体的三取代芳基胍文库，进一步证明了该连接基的适用范围和局限性。
