Application of 3,4-dihydro-3-hydroxy-4-oxy-1,2,3-benzotriazine_Kain Industrial Additive

Background and overview^[1]

3,4-Dihydro-3-hydroxy-4-oxo-1,2,3-benzotriazine is a heterocyclic organic compound and a polypeptide synthesis condensation agent, referred to as HOOBt. Compared with urea salts such as HBTU and HATU (phosphorus-(7-azabenyltriazol-1-yl)-1,1,3,3-tetramethylurea hexafluorophosphate), HOOBt is not only low in cost, but also more important What is unique is that in the condensation reaction, there is no side reaction in which urea salts such as HBTU and HATU react with primary amines to form guanidinium salts. Therefore, HOOBt is an ideal condensation reagent for peptide synthesis.

Preparation^[1]

Dissolve 48g of sodium hydroxide in 300ml of water, cool to room temperature, add a total of 41.6g of hydroxylamine hydrochloride in batches while stirring, and add dropwise a mixture of 38.7ml of 2-aminobenzoic acid methyl ester and 30ml of methanol. React at room temperature for 3 days. Distill under reduced pressure until white sodium salt precipitates (about 100ml of mother liquor at this time). After cooling, the solution was filtered, and the precipitate was washed with petroleum ether and dried to obtain a total of 38 g of white solid.

Dissolve the white solid obtained in 60ml concentrated hydrochloric acid and dilute with 700ml water. With stirring at a controlled temperature of 0-5°C, sodium nitrite solution (16g sodium nitrite dissolved in 500ml of water) was added dropwise and diazotized. The solution was continued to stir for 45 min at room temperature. The solution was filtered and dried to obtain a total of 22.8g of 3-hydroxy-1,2,3-benzotriazin-4(3H)-one as a white solid.

Apply^[2-3]

CN200810117886.2 reports an inhibitor to prevent sulfate-reducing bacteria corrosion, which can be used in oil wells to prevent sulfate-reducing bacteria corrosion. The characteristics are: weight ratio of each component: a. Aqueous solution of polypeptide condensation reagent (3-hydroxy-1,2,3-benzotriazin-4(3H)-one, HOOBt) C7H5N3O2 with a content of 0.05%: 13.5~ 18.0%; b. Magnesium sulfate MgSO4·7H2O: 2.0~5.0%; c. Sodium sulfate: 1.5~4.5%; d. Yeast extract: 0.05~0.2%; e. Dipotassium hydrogen phosphate K2HPO4: 0.5~2.0%; f .Vitamin C: 0.05~0.5%; g. The rest is water. The effect is: using the inhibitor prepared by this method to prevent sulfate-reducing bacteria from corrosion, in the process of preventing sulfate-reducing bacteria in oil wells, under the condition of adding 0.05~0.1%, the content of sulfate-reducing bacteria in the system is less than 25 pieces/ml.

CN201310028587.2 provides a porous material loaded with a polypeptide condensation agent. The polypeptide condensation agent is adsorbed in the porous material. The polypeptide condensation agent is HOAT or HOBT or 3-hydroxy-1,2,3-benzotriazine. -4(3H)-ketone, the porous material is diatomite or molecular sieve or silica gel. The present invention provides a method for preparing the above-mentioned porous material loaded with a polypeptide condensation agent, which includes the step of adsorbing the polypeptide condensation agent to the porous material. The adsorption is to dissolve the polypeptide condensation agent in an organic solvent and then uniformly disperse it in the porous material. and porous material surfaces. In addition, the present invention further provides the use of porous materials loaded with polypeptide condensation agents for catalyzing the reaction of organic amines and acids to form amide bonds. The porous material provided by the invention can solve the safety problems of the polypeptide condensation agent during storage or transportation, has simple preparation, low cost, good thermal stability, can directly participate in the reaction without desorption, and does not affect its Product yield, has very good application prospects.

Main reference materials

[1] [Chinese invention] CN200510126588.6 Synthesis method of polypeptide synthesis condensation agent 3-hydroxy-4-oxy-3,4-dihydro-1,2,3-benzotriazine

[2] CN200810117886.2 An inhibitor to prevent corrosion of sulfate reducing bacteria

[3] CN201310028587.2 Porous material loaded with polypeptide condensation agent, preparation method and use thereof