Title of article :
Mechanistic studies of DCC/HOBt-mediated reaction of 3-phenylpropionic acid with benzyl alcohol and studies on the reactivities of ‘active ester’ and the related derivatives with nucleophiles
Author/Authors :
Md. Chanmiya Sheikh، نويسنده , , Shunsuke Takagi، نويسنده , , Toshiaki Yoshimura، نويسنده , , Hiroyuki Morita، نويسنده ,
Issue Information :
هفته نامه با شماره پیاپی سال 2010
Abstract :
Despite of the extensive study for peptide synthesis, DCC-mediated esterification is left still unclear. Therefore, DCC- and DCC/HOBt-mediated reactions of 3-phenylpropionic acid (1) with benzyl alcohol were carried out under several mechanistic considerations. Further, in order to determine the reactivities of the so-called ‘active esters’ compounds changing the substituents bearing carbonyl and related derivatives group for the purpose of the development of new class of non-symmetry cross-linkers, we have studied the reaction of model compounds, N-(3-phenylpropionyloxy)benzotriazole (6), N-(3-phenylpropionyloxy)phthalimide (7), 3-phenylpropionyloxybenzothiazole (8), and N-(3-phenylpropionyl)benzotriazole (9) with various nucleophiles under similar conditions were carried out for the comparison. It was revealed to exhibit the order of 6>>8>9>7.
Keywords :
DCC , Hydroxybenzotriazole , ‘Active ester’ derivatives , Reactivity , Base-catalyzed esterification
Journal title :
Tetrahedron
Journal title :
Tetrahedron