Polypeptide synthetic condensation agent 3-hydroxy-4-oxy-3,4-dihydro-1,2,3-benzotriazozine synthesizing method

A technique for synthesizing benzotriazoxide and polypeptides, applied in organic chemistry and other fields, can solve the problems of low condensation efficiency, racemization, and easy rearrangement of intermediates, and achieve the effects of less side reactions, low toxicity, and easy separation

Inactive Publication Date: 2007-06-13
LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Application Information

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Problems solved by technology

However, in the presence of triethylamine, the DCC condensation active polypeptide intermediate is easy to rearrange, or there is a danger of racemization, resulting in low condensation efficiency

Method used

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  • Polypeptide synthetic condensation agent 3-hydroxy-4-oxy-3,4-dihydro-1,2,3-benzotriazozine synthesizing method
  • Polypeptide synthetic condensation agent 3-hydroxy-4-oxy-3,4-dihydro-1,2,3-benzotriazozine synthesizing method
  • Polypeptide synthetic condensation agent 3-hydroxy-4-oxy-3,4-dihydro-1,2,3-benzotriazozine synthesizing method

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Embodiment 1

[0031] Dissolve 48g of sodium hydroxide in 300ml of water, cool to room temperature, add 41.6g of hydroxylamine hydrochloride in batches under stirring, and add dropwise a mixture of 38.7ml of methyl 2-aminobenzoate 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, filter with suction, wash the precipitate with petroleum ether, and dry to obtain a total of 38 g of white solid.

[0032] The obtained white solid (1) was dissolved in 60ml of concentrated hydrochloric acid and diluted with 700ml of water. Under stirring at a temperature of 0-5°C, sodium nitrite solution (16g of sodium nitrite dissolved in 500ml of water) was added dropwise for diazotization. The solution was stirred and reacted for 45 min at room temperature. The solution was filtered, and the precipitate was dried to obtain 22.8 g of white solid (2).

[0033] IR data charac...

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Abstract

This invention discloses a composing method of polypeptide synthesis condensing agent that is 3-hydroxide radical-4-oxygen-3,4-dihydro-1,2,3- benzotriazin. This method uses methyl anthranilate as initiation factors. Target product is obtained by three step reaction with easily obtained raw material that is low poison. This invention has characteristics such as raw material is easily obtained, route is simple, noxious property is low, side reaction is little, it easily attributes, overall yield is suitable.

Description

Technical field: [0001] The invention relates to a method for synthesizing polypeptide synthesis condensing agent 3-hydroxyl-4-oxo-3,4-dihydro-1,2,3-benzotriazoxide (HOOBt). Background technique: [0002] In the solid-phase synthesis reaction of polypeptide or peptide nucleic acid, the choice of condensing agent not only affects the condensation yield, but also may affect the configuration of the target. Therefore, choosing a condensing agent with high activity, low side reaction, easy separation and low cost has always been the key to solid-phase peptide synthesis. [0003] In 1955, Sheehan and Hess used N,N-dicyclohexylcarbodiimide (DCC) for the first time in peptide synthesis and achieved good results. However, in the presence of triethylamine, the DCC condensation active polypeptide intermediate is easy to rearrange, or there is a danger of racemization, resulting in low condensation efficiency. [0004] In 1966, Wiinsch and Dress found that the addition of hydroxysucc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D253/08
Inventor 刘相陈淼
Owner LANZHOU INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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