Synthesis of amino acid derivatives of 4-(1-adamantyl)benzoic acid obtained by transition metal ion catalyzed oxidation of 4-(1-adamantyl)toluene

Abstract

An efficient synthesis of 4-(1-adamantyl)benzoic acid based on transition metal ion catalyzed oxidation of 4-(1-adamantyl)toluene has been developed. As a catalytic system, cobalt–manganese bromide with addition of manganese acetate was used. A series of amino acid derivatives of 4-(1-adamantyl)benzoic acid was then synthesized and characterized. These derivatives are novel intermediates potentially useful in the design of therapeutically active peptidomimetics with improved pharmacokinetic and pharmacodynamic parameters.