Date of Original Version
Biomedical and Pharmaceutical Sciences
Aminomethyl polystyrene resin was reacted with 4-(5‘-formyl-2‘-hydroxyphenyl)benzoic acid and 4-(5‘-formyl-2‘-hydroxyphenyl)phenyl propionic acid, respectively, in the presence of 1-hydroxybenzotriazole and 1,3-diisopropylcarbodiimide to yield polymer-bound benzaldehydes. The phenolic group in resins was acetylated with acetic anhydride to afford two polymer-bound 4-acetoxybenzaldehydes. The reductive amination of polymer-bound linkers by amines and sodium triacetoxyborohydride, followed by sulfonylation with arylsulfonyl chloride derivatives in the presence of pyridine and the cleavage with TFA/DCM/H2O, produced pure sulfonamides.
Kumar, A., Ye, G., Ahmadibeni, Y., & Parang, K. (2006). Synthesis of Polymer-Bound 4-Acetoxy-3-phenylbenzaldehyde Derivatives: Applications in Solid-Phase Organic Synthesis. J. Org. Chem. 71(20), 7915-7918. doi: 10.1021/jo061328z
Available at: https://doi.org/10.1021/jo061328z