3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one (DEPBT): a new coupling reagent with remarkable resistance to racemization.
[formula: see text] 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.
Li
H
H
Department of Chemistry and Biochemistry, University of California at San Diego, La Jolla 92093, USA.
Jiang
X
X
Ye
Y H
YH
Fan
C
C
Romoff
T
T
Goodman
M
M
D000577:Amides / Q000737:chemistry; D010755:Organophosphates / Q000737:chemistry*; D013237:Stereoisomerism; D014227:Triazines / Q000737:chemistry*
C410327:3-(diethoxyphosphoryloxy)-1,2,3-benzotriazin-4(3H)-one; D000577:Amides; D010755:Organophosphates; D014227:Triazines