219803-84-6Relevant academic research and scientific papers
Acetophenone-based linker for solid phase synthesis of secondary amides and sulfonamides on the multipin(TM) support
Bui, Chinh T.,Bray, Andrew M.,Ercole, Francesca,Pham, Yen,Rasoul, Firas A.,Maeji, N. Joe
, p. 3471 - 3474 (1999)
A new and simple linker has been developed for synthesis of secondary amides and sulfonamides. This application is based on the reductive amination reaction between the acetophenone subunit of the linker and a wide range of primary amines including aliphatic and aromatic amines. Cleavage is effected under mild acidic conditions (20% TFA/DCM) to release the products in good yield and purity.
Efficiencies of reductive amination reactions on different solid supports
Bui, Chinh T.,Rasoul, Firas A.,Ercole, Francesca,Pham, Yen,Maeji, N. Joe
, p. 9279 - 9282 (1998)
Reductive amination on resins derivatized with 5-(4-formyl-3,5- dimethoxyphenoxy)valeric acid linker (Barany linker, 1)1 has been reported to be less effective than on resin derivatized with its monomethoxy analog (2)2 due to steric hindrance of the extra methoxy functional group within the molecule.3 A study of these linkers indicate that the origins of such data is also related to the spacer and solid support used in the study. Depending on the linker, spacer and solid phase, yields from 10% to 75% were obtained under exactly the same reaction conditions.
