O-N Intramolecular alkoxycarbonyl (carbonate-carbamate) migration was found to occur as a common reaction of hydroxyamino acids under mild basic aqueous conditions with no formation of side products. Carbonate protective groups migrate to produce amino-protected carbamate derivatives of hydroxyamino acids with high efficiency and purity.
Department of Medicinal Chemistry, Center for Frontier Research in Medicinal Science, 21st COE Program, Kyoto Pharmaceutical University, Yamashina-ku, Kyoto 607-8412, Japan.