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%.
Kita
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R
Department of Chemistry, University of California, Berkeley, CA 94720-1460, USA.
Svec
F
F
Fréchet
J M
JM
D000588:Amines / Q000737:chemistry; D020650:Combinatorial Chemistry Techniques; D006827:Hydantoins / Q000138:chemical synthesis*; D008689:Methacrylates; D011092:Polyethylene Glycols / Q000138:chemical synthesis*; D011108:Polymers; D012117:Resins, Synthetic / Q000138:chemical synthesis
D000588:Amines; D006827:Hydantoins; D008689:Methacrylates; D011108:Polymers; D012117:Resins, Synthetic; C450003:poly(ethylene glycol) methacrylate polymer; D011092:Polyethylene Glycols