Optimisation of conditions for O-benzyl and N-benzyloxycarbonyl protecting group removal using an automated flow hydrogenator

Abstract

A versatile, fully automated flow hydrogenator has been developed that is able to perform sequential flow optimisation experiments, flow library hydrogenation, or iterative scale-up hydrogenation. The behaviour of a palladium catalyst in effecting removal of O-benzyl and N-benzyloxycarbonyl protecting groups has been investigated. Significant observations relating to maintaining optimal throughput are reported. A small library of peptidic derivatives has been deprotected in high yield and purity. © 2007 Wiley-VCH Verlag GmbH & Co. KGaA,.