Facile synthesis of new amine high-loaded poly(meth)acrylamide-based resins for solid phase peptide synthesis

Two methods for the ready preparation of some protected primary amine-functionalized (meth)acrylamide derviatives from amino halides or amino alcohols are described. The (meth)acryloyl moiety is introduced either in the last step from unsymmetrically N,N'-disubstituted diamines or, more simply, in the first step, but that demands a special work-up of the reaction mixture in order to prevent polymerization. Both methods are complementary. Reverse phase suspension polymerization of the title compounds with N-acryloylpyrrolidine and N,N'-ethylenebis(acrylamide) directly affords new beaded, high-loaded amine-functionalized resins for solid phase peptide synthesis.