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Volume 4, Issue 3, 1998, pp. 155-163

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

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.

linkers, N-alkylamides, reductive amination, solid-phase synthesis

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