一种用于合成羧酰胺和磺酰胺的含氟标记的酸不稳定保护基。

A fluorous-tagged, acid-labile protecting group for the synthesis of carboxamides and sulfonamides.

作者信息

Villard Anne-Laure, Warrington Brian H, Ladlow Mark

机构信息

GlaxoSmithKline Cambridge Technology Centre, University Chemical Laboratory, Lensfield Road, Cambridge, CB2 1EW, UK.

出版信息

J Comb Chem. 2004 Jul-Aug;6(4):611-22. doi: 10.1021/cc0499338.

DOI:10.1021/cc0499338

PMID:15244423

Abstract

A new acid-labile, fluorous-tagged protecting group that facilitates the preparation of carboxamides and sulfonamides by parallel solution-phase synthesis is introduced. Its use is exemplified by the preparation of a 27-member library of biaryl sulfonamides and an 18-member library of biaryl carboxamides. Intermediates were purified by solid-phase extraction over reversed-phase fluorous silica gel to afford library members in high yields and purities (>95%) without the need for column chromatographic purification.

摘要

引入了一种新型的对酸不稳定、带有氟标签的保护基团，该基团有助于通过平行溶液相合成制备羧酰胺和磺酰胺。通过制备一个包含27个成员的联芳基磺酰胺文库和一个包含18个成员的联芳基羧酰胺文库来举例说明其用途。中间体通过反相氟硅胶进行固相萃取纯化，从而以高收率和高纯度（>95%）获得文库成员，无需柱色谱纯化。