57115-46-5

Usage

Uses

Used in Pharmaceutical and Biotechnology Industries:
1-Hydroxy-7-azabenzotriazole is utilized as a coupling agent for enhancing the efficiency of peptide bond formation, thereby facilitating the synthesis of complex peptides. Its low racemization tendency ensures the preservation of peptide integrity during the synthesis process.
Used in Solid-Phase Peptide Synthesis:
In the context of solid-phase peptide synthesis, HATU is employed to improve the yield of peptide bonds and reduce the occurrence of epimerization, which can compromise the structural and functional integrity of the synthesized peptides.
Used in Antimicrobial Applications:
1-Hydroxy-7-azabenzotriazole has demonstrated antimicrobial activity against certain bacteria and fungi, broadening its potential applications in various fields, including medicine and microbiology, where it can be leveraged to combat microbial infections.
Used in Organic Synthesis:
Beyond peptide synthesis, HATU's reactivity and solubility make it a reliable agent in the synthesis of a wide range of organic molecules, contributing to the advancement of organic chemistry and the development of new compounds with diverse applications.

Upstream product

• 110-91-8 morpholine 
• 110-89-4 piperidine 
• 5470-18-8 2-Chloro-3-nitropyridine 
• 291274-20-9 1-methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine 

Downstream Products

• 1027487-68-8 2-benzyloxycarbonylamino-2-methyl-propionic acid [1,2,3]triazolo[4,5-b]pyridin-1-yl ester 
• 291274-20-9 1-methoxy-1H-[1,2,3]triazolo[4,5-b]pyridine 
• 273-34-7 v-triazolo<4,5-b>pyridine 
• 1417187-40-6 tert-butyl N-(tert-butoxycarbonyl)-O-[( 1H-1,2,3-triazolo[5,4-b]pyridin-1-yloxy)methyl]-D-tyrosinate 

Relevant academic research and scientific papers

Synthesis of N-(2-Hydroxyaryl)benzotriazoles via Metal-Free O-Arylation and N-O Bond Cleavage

A metal-free method for synthesis of N-(2-hydroxyaryl)benzotriazoles via O-arylation of N-hydroxybenzotriazoles with readily available diaryliodonium salts and sequential N-O bond cleavage under mild conditions has been developed. The [3,3]-rearrangement of N-O bond cleavage could take place on the N instead of C atom. The reaction was compatible with diverse functional groups and a new type of P,N-ligand was synthesized in three steps.

Mild and general access to diverse 1H-benzotriazoles via diboron-mediated N-OH deoxygenation and palladium-catalyzed C-C and C -N bond formation

Benzotriazoles are a highly important class of compounds with broad-ranging applications in such diverse areas as medicinal chemistry, as auxiliaries in organic synthesis, in metallurgical applications, in aircraft deicing and brake fluids, and as antifog agents in photography. Although there are numerous approaches to N-substituted benzotriazoles, the essentially one general method to N-unsubstituted benzotriazoles is via diazotization of ortho -phenylenediamines, which can be limited by the availability of suitable precursors. Other methods to N-unsubstitued benzotriazoles are quite specialized. Although reduction of 1-hydroxy-1 H-benzotriazoles is known, the reactions are not particularly convenient or broadly applicable. This presents a limitation for easy access to and availability of diverse benzotri-ACHTUNGTRENUNGazoles. Herein, we demonstrate a new, broadly applicable method to diverse 1H-benzotriazoles via a mild diboron reagent-mediated deoxygenation of 1-hydroxy-1H-benzotriazoles. We have also evaluated sequential deoxygenation and Pd-mediated C-C and C-N bond formation as a one-pot process for further diversification of the benzotriazole moiety. However, the results indicated that purification of the deoxygenation product prior to the Pd-mediated reaction is critical to the success of such reactions. The overall chemistry allows for facile access to a variety of new benzotriazoles. Along with the several examples presented, a discussion of the advantages of the approaches is described, as is also a possible mechanism for the deoxygenation process.

Spectrophotometric determination of pKa's of 1-Hydroxybenzotriazole and oxime derivatives in 95% acetonitrile-water

1-hydroxybenzotriazole derivatives are used with carbodiimide as additives to generate active esters during peptide bond formation. They are also used as additives during the peptide bond formation. Dissociation constants of the 1-hdroxybenzotriazole (HOBt) and its derivatives, 1- hydroxy-6- chlorobenzotriazole, 1-hydroxy-6-trifluoromethylbenzotriazole, 1-hydroxy-6-nitrobenzotriazole were determined spectrophotometrically in 95% acetonitrile-water. In addition, 7-aza-1- hydroxybenzotriazole (7-HOAt) and 4-aza-1-hydroxybenzotriazole (4-HOAt) were also studied. Recently, oxyma was reported as a good replacement for the benzotriazole derivatives. As alcoholic components of active esters, the oximes seem to be good leaving groups. Therefore it was expected, that the strongly acidic and nucleophilic oximes, which possess electron-withdrawing groups in the molecule, are suitable as additives during the peptide bond formation. The dissociation constant of some oximes,such as diethyl 2-(hydroxyimino)malonate, ethyl 2-cyano-2-(hydroxyimino) acetate (oxyma), hydroxycarbonimidoyl dicyanide and N-hydroxypicolinimidoyl cyanide in 95% acetonitrile-water are reported.

Synthesis and aminolysis of N,N-diethyl carbamic ester of HOBt derivatives

The reaction of N,N-diethyl carbamates of 1H-[1,2,3]triazolo[4,5-b]pyridin- 1-ol (4-HOAt) 7, 3H-[1,2,3]triazolo[4,5- b]pyridin-3-ol (7-HOAt) 8, 1H-benzo[d][1,2,3]triazol-1-ol (HOBt) 9, 6-chloro-1H-benzo[d][1,2,3]triazol-1-ol (Cl- HOBt) 10, 6-(trifluoromethyl)-1H-benzo[d][1,2,3]triazol-1-ol (CF3 3-HOBt) 11, and 6-nitro-1H-benzo[d][1,2,3]triazol- 1-ol (NO2 2-HOBt) 12 with morpholine and piperidine in CH3CN underwent acyl nucleophilic substitution to give the corresponding carboxamide derivatives. The reactants and products were identified by elemental analysis, IR and NMR. We measured the kinetics of these reactions spectrophotometrically in CH3 3CN at a range of temperatures. The rates of morpholinolysis and piperidinolysis were found to fit the Hammett equation and correlated with s-Hammett values. The values were 1.44 - 1.21 for morpholinolysis and 1.95 - 1.72 for piperidinolysis depending on the temperature. The Bronsted-type plot was linear with a βlg = -0.49 ± 0.02 and -0.67 ± 0.03. The kinetic data and structure-reactivity relationships indicate that the reaction of 9-12 with amines proceeds by a concerted mechanism. The deviation from linearity of the correlation ?H# vs. ?S# and plot of logkpip vs. logkmorph and Bronsted-type correlation indicate that the reactions of amines with carbamates 7 and 8 is attributed to the electronic nature of their leaving groups.

Synthesis and morpholinolysis of N,N-diethyl carbamate derivatives of 4- HOAt, 7-HOAt and HOBt

N,N-Diethyl carbamates of 1-hydroxy-7-azabenzotriazole (7-HOAt), 1-hydroxy-4-azabenzotriazole (4-HOAt), 1-hydroxybenzotriazole (HOBt), and 1-hydroxypyrrolidine-2,5-dione have been synthesised. The reactivities of these active esters have been determined by studying the kinetics and mechanism of their morpholinolysis in acetonitrile at different temperatures.

Comparison of the effects of 5- and 6-HOAt on model peptide coupling reactions relative to the cases for the 4- and 7-isomers

(equation presented) Synthesis of 5- and 6-HOAt has completed the full set of the four HOAt isomers derived from HOBt by insertion of a single nitrogen atom in the benzenoid nucleus. Comparison of the reactivity of all four isomers in model peptide coupling reactions has confirmed the unique character of the 7-isomer in promoting selectivity and maintaining configuration at the reactive carboxylic acid residue.

Azahydroxybenzotriazoles and derivatives thereof for peptide coupling reactions

This invention relates to a process for forming an amide or an ester from a reaction between an amine or an alcohol, respectively and an acylating derivative of a carboxylic acid, in the presence of an effective amount of a compound having the formula: STR1 and N-oxides thereof and salts thereof.