Solid-phase synthesis of acyclic and cyclic amino acid derived urea peptidomimetics using phoxime resin

The use of Phoxime resin 2 (phosgenated p-nitrophenyl(polystyrene)ketoxime) in the synthesis of acyclic and heterocyclic amino acid derived ureas is d escribed. Resin 2 was previously shown to be a useful precursor in the soli d-phase preparation of nonsymmetric ureas from thermolysis of corresponding primary amine oxime carbamates and subsequent trapping with an amine in so lution. Generation of functionalized polymer-supported primary amine oxime carbamates (3 and 9) for further diversification was accomplished by additi on of amino acids or substituted hydrazines to resin 2. The use of these fu nctionalized oxime carbamate resins for the generation of acyclic alpha-ure idoacetamides 5, 3-aminohydantoins 7, and 1,2,4-triazine-3,6-diones 8 is su itable for combinatorial library generation.