title: Kinetics study of amine cleavage reactions of various resin-bound thiophenol esters from marshall linker.
abstract: The kinetics of cleavage reactions of seven resin-bound thiophenol esters with three amines has been studied by single-bead FTIR. The reactivity of these seven thiophenol esters was dependent on their structures and could be summarized as follows: 5-benzimidazolecarboxylic thiophenol ester > alkyl thiophenol ester > aromatic thiophenol ester. The reactivity of three amines was summarized as follows: n-butylamine > 3,4-dimethoxyphenethylamine > 1-piperonylpiperazine. The rate of the cleavage reaction increased 2-fold per 10 degrees C rise in reaction temperature. Oxidation of the thiophenol linker increased the rate of the cleavage reaction by 580-fold.
authors.affiliation: ChemRx Division, Discovery Partners International, Inc., 385 Oyster Point Boulevard, South San Francisco, California 94080, USA.
authors.forename: Liling
authors.initials: L
authors.lastname: Fang
authors.forename: Michael
authors.initials: M
authors.lastname: Demee
authors.forename: Teresa
authors.initials: T
authors.lastname: Sierra
authors.forename: Tushar
authors.initials: T
authors.lastname: Kshirsagar
authors.forename: Azim A
authors.initials: AA
authors.lastname: Celebi
authors.forename: Bing
authors.initials: B
authors.lastname: Yan