Hydrophilic polymer supports for solid-phase synthesis: preparation of poly(ethylene glycol) methacrylate polymer beads using "classical" suspension polymerization in aqueous medium and their application in the solid-phase synthesis of hydantoins.

Abstract

Lightly cross-linked hydrophilic polymer beads representing new types of supports for solid-phase synthesis have been prepared from commercial oligoethylene glycol monomethacrylates using an aqueous suspension polymerization process and specifically designed polymerization mixtures. These beads swell extensively in solvents with a wide range of polarities from dichloromethane, tetrahydrofuran, and water to dimethylformamide, and they enable high functional loadings of 1.2-1.8 mmol g(-1). Their ability to serve as supports was demonstrated in the model solid-phase synthesis of a small library of hydantoins. This four-step synthesis using primary amines readily affords yields of over 70%.