Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the MultipinTM approach
Chinh T. Bui, Andrew M. Bray, Yen Pham, Rhonda Campbell, Francesca Ercole, Firas A. Rasoul, N. Joe Maeji
Abstract
The 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany) linker and its
monomethoxy analog were applied to the MultipinTM method of
solid phase synthesis. A comparative assessment of reductive amination
and cleavage of these linkers under conditions of multiple synthesis
indicated that both were applicable to a broad range of primary amines
including aniline and 4-nitroaniline. Apart from the greater lability of
the dimethoxy version under TFA cleavage, there was no observable
advantage of one linker over the other within the described experiment.
Keywords
linkers, N-alkylamides, reductive amination, solid-phase synthesis
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