Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin approach.
The 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid (Barany) linker and its monomethoxy analog were applied to the Multipin 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.
Bui
C T
CT
Chiron Technologies Pty Ltd., Clayton, VIC, Australia. chinh_thien_bui@cc.chiron.com
Bray
A M
AM
Pham
Y
Y
Campbell
R
R
Ercole
F
F
Rasoul
F A
FA
Maeji
N J
NJ
D000586:Amination; D001547:Benzaldehydes / Q000138:chemical synthesis* / Q000378:metabolism*; D002851:Chromatography, High Pressure Liquid; D010421:Pentanoic Acids / Q000737:chemistry*; D010455:Peptides / Q000138:chemical synthesis* / Q000302:isolation & purification; D014631:Valerates / Q000138:chemical synthesis* / Q000378:metabolism*
C408391:5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid; C408392:5-(4-formyl-3-methoxyphenoxy)valeric acid; D001547:Benzaldehydes; D010421:Pentanoic Acids; D010455:Peptides; D014631:Valerates; C038780:n-pentanoic acid