title: Comparative study of reductive amination reaction on 5-(4-formyl-3,5-dimethoxyphenoxy)valeric acid and its monomethoxy analog using the Multipin approach.
abstract: 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.
authors.affiliation: Chiron Technologies Pty Ltd., Clayton, VIC, Australia. chinh_thien_bui@cc.chiron.com
authors.forename: C T
authors.initials: CT
authors.lastname: Bui
authors.forename: A M
authors.initials: AM
authors.lastname: Bray
authors.forename: Y
authors.initials: Y
authors.lastname: Pham
authors.forename: R
authors.initials: R
authors.lastname: Campbell
authors.forename: F
authors.initials: F
authors.lastname: Ercole
authors.forename: F A
authors.initials: FA
authors.lastname: Rasoul
authors.forename: N J
authors.initials: NJ
authors.lastname: Maeji
mesh_terms: 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*
chemical_list: 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