165534-43-0

Usage

Uses

Used in Pharmaceutical Industry:
DEPBT is used as a peptide coupling reagent for the synthesis of peptides. Its resistance to racemization ensures the production of peptides with the correct stereochemistry, which is essential for their biological activity and therapeutic efficacy.
Used in Research and Development:
In the field of research and development, DEPBT is utilized for the synthesis of complex peptides and peptidomimetics. Its effectiveness in promoting amide bond formation and preventing racemization makes it a valuable tool for the development of novel peptide-based drugs and therapeutic agents.
Used in Organic Chemistry:
DEPBT is also employed in organic chemistry as a reagent for the formation of carbon-nitrogen bonds. Its ability to promote amide bond formation makes it useful in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and other specialty chemicals.

InChI:InChI=1/C11H14N3O5P/c1-3-17-20(16,18-4-2)19-14-11(15)9-7-5-6-8-10(9)12-13-14/h5-8H,3-4H2,1-2H3

Synthetic route

diethyl chlorophosphate (814-49-3) + 3-hydroxy-3,4-dihydrobenzotriazine-4-one (28230-32-2) → 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0)

Conditions	Yield
With triethylamine In dichloromethane for 3h;	82%
With triethylamine In dichloromethane at 0℃; for 3h;	82%

phosphonic acid diethyl ester (762-04-9) + 3-hydroxy-3,4-dihydrobenzotriazine-4-one (28230-32-2) → 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0)

Conditions	Yield
With triethylamine In dichloromethane; benzene for 4h;	57%

Z-Aib-OH (15030-72-5) + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → 2-benzyloxycarbonylamino-2-methyl-propionic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester (654651-46-4)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 37℃;

N-benzoyl-(R)-methylpiperazine hydrochloride + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → 1H-indol-1-amine (53406-38-5)

Conditions	Yield
With N-ethyl-N,N-diisopropylamine In water; N,N-dimethyl-formamide

3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → 2-oxo-2-(1H-pyrrolo[3,2-c]pyridin-3-yl)-acetamide (1378780-41-6)

Conditions	Yield
With ammonia; N-ethyl-N,N-diisopropylamine In 1,4-dioxane; N,N-dimethyl-formamide

potassium 2-pyrrolecarboxaldehyde-4-oxoacetate + N-benzoylpiperazine hydrochloride (56227-55-5, 79332-89-1) + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → N-benzoyl-N'-[(2-carboxaldehyde-pyrrole-4-yl)-oxoacetyl]-piperazine

Conditions	Yield
With triethylamine In water; N,N-dimethyl-formamide
With triethylamine In water; N,N-dimethyl-formamide

(7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-oxo-acetic acid (791053-66-2) + phenyl(piperidin-4-ylidene)acetonitrile (676490-69-0) + N-ethyl-N,N-diisopropylamine (7087-68-5) + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → {1-[2-(7-chloro-1H-pyrrolo[3,2-b]pyridin-3-yl)-2-oxo-acetyl]-piperidin-4-ylidene}-phenyl-acetonitrile (676490-39-4)

Conditions	Yield
In ethyl acetate; N,N-dimethyl-formamide

C42H51N7O10S5Si + C35H47N5O8S2Si + 3-[(diethoxyphosphinyl)oxy]-1,2,3-benzotriazin-4(3H)-one (165534-43-0) → C77H96N12O17S7Si2 + C81H105N12O20PS7Si2

Conditions	Yield
With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 25h; Overall yield = 14.7 mg;

Upstream product

• 762-04-9 phosphonic acid diethyl ester 
• 28230-32-2 3-hydroxy-3,4-dihydrobenzotriazine-4-one 
• 814-49-3 diethyl chlorophosphate 

Downstream Products

• 654651-46-4 2-benzyloxycarbonylamino-2-methyl-propionic acid 4-oxo-4H-benzo[d][1,2,3]triazin-3-yl ester 
• 53406-38-5 1H-indol-1-amine 

Relevant academic research and scientific papers

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.

A novel organophosphorus compound as a coupling reagent for peptide synthesis

3-(Diethoxyphosphoryloxy)-1,2,3-benzotriazin-4 (3H)-one 1 is a new organophosphorus compound which can be used as an efficient coupling reagent for peptide synthesis by either solution or solid phase coupling.