American Chemical Society
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3-(Diethoxyphosphoryloxy)-1,2,3- benzotriazin-4(3H)-one (DEPBT):  A New Coupling Reagent with Remarkable Resistance to Racemization

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journal contribution
posted on 1999-05-24, 00:00 authored by Haitao Li, Xiaohui Jiang, Yun-hua Ye, Chongxu Fan, Todd Romoff, Murray Goodman
The new crystalline phosphate reagent 3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT) mediates amide bond formation with a remarkable resistance to racemization. Comparative racemization studies were carried out and DEPBT proved to be superior to typical phosphonium and uronium coupling reagents. DEPBT is easily prepared and is exceedingly stable with a shelf life of months at room temperature. The advantageous properties of DEPBT render it a useful and unique addition to the arsenal of coupling reagents.