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

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%.