Synthesis of hydantoins via N, N˘-ureas derived from polymer-bound amino acids

M. Bauser, M. Winter, C. A. Valenti, G. Jung
University of Tübingen, Institute of Organic Chemistry, Auf der Morgenstelle 18, D-72076 Tübingen, Germany

K.-H. Wiesmüller
Nmi Reutlingen, Eberhardstr. 29, D-72768 Reutlingen, Germany

Abstract
Starting from carboxy-linked amino acids on trityl functionalized polystyrene resin a highly efficient solid-phase synthesis of hydantoins via N, N˘-ureas was elaborated. The polymer-bound hydantoins can be used as scaffolds for further combinatorial transformations, such as alkylation. Cleavage from the resins yielded the corresponding hydantoins in good yields and purities as shown by ESI-MS and HPLC.

Keywords
automated synthesis, combinatorial chemistry, hydantoins, imidazolidinediones, solid phase synthesis