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Preparation method of dibutylboron trifluoromethanesulfonate

A technology of dibutyl boron trifluoromethanesulfonate and organic solvents, which is applied in the field of medicinal chemistry and can solve the problems of inability to realize large-scale production and high cost

Pending Publication Date: 2021-09-14
SUZHOU IBIO TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, the key reagent of dibutylboron trifluoromethanesulfonate is extremely expensive in the current market, which also leads to the inability to achieve large-scale production of Dap synthesis

Method used

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  • Preparation method of dibutylboron trifluoromethanesulfonate
  • Preparation method of dibutylboron trifluoromethanesulfonate

Examples

Experimental program
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Effect test

Embodiment 1

[0034]

[0035] (n-Bu is n-butyl)

[0036] Under an inert nitrogen atmosphere, the BH 3 ·SMe 2 Soluble in an aprotic organic solvent, the aprotic organic solvent is ether, tetrahydrofuran, n-hexane, etc., preferably n-hexane, the temperature of the system is raised to 20-60°C, preferably 45-50°C, and then 10% n-butene hexane The alkane solution is added to the constant pressure dropping funnel, and slowly added dropwise to the system, wherein, the solvent volume selection range: 1 to 10 parts by volume, preferably 3 parts by volume; BH 3 ·SMe 2 The molar ratio to n-butene is 1:3 to 1:10, and this range includes the numerical range of any subrange therein, and non-limiting examples are 1:3 and 1:4. The temperature of the whole reaction process is controlled at 0-60°C, preferably 45-50°C. After the dropwise addition, the temperature of the system is maintained at 45-50°C for 1-8 hours, preferably 1-6 hours. After the reaction is completed, the temperature is lowered to -2...

Embodiment 2

[0038] (n-Bu is n-butyl)

[0039] Under an inert gas nitrogen atmosphere, the n-Bu 3B is dissolved in an aprotic organic solvent, and the aprotic organic solvent is dichloromethane, tetrahydrofuran, n-hexane, etc., preferably dichloromethane, and the temperature of the system is reduced to -20~0°C, preferably -5~0°C, and three Fluoromethanesulfonic acid is dissolved in dichloromethane, added to the constant pressure dropping funnel, and slowly added dropwise to the system, wherein, the solvent volume selection range: 1 to 10 parts by volume, preferably 2 parts by volume; n-Bu 3 The molar ratio of B to trifluoromethanesulfonic acid is 1:1 to 1:10, and this range includes the numerical range of any subrange therein, and non-limiting examples are 1:1 and 1:2. The temperature of the whole reaction process is controlled at -5 ~ 10 ° C, preferably 0 ~ 5 ° C, after the dropwise addition, maintain this temperature for 0 ~ 0.5 hours, then raise the temperature to 20 ~ 40 ° C, prefer...

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Abstract

The invention provides a preparation method of dibutylboron trifluoromethanesulfonate. The preparation method comprises the following steps: reacting borane dimethyl sulfide with n-butene to generate tributyl boron, and reacting tributyl boron with trifluoromethanesulfonic acid to generate the dibutylboron trifluoromethanesulfonate. The preparation method provided by the invention can be used for efficiently preparing dibutyl boron trifluoromethanesulfonate, and the yield is up to 89-91%, so that large-scale production of Dap synthesis is realized.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry, and in particular relates to a preparation method of dibutylboron trifluoromethanesulfonate. Background technique [0002] Dolastoxin, one of the marine biotoxins [1] It is a linear depsipeptide natural cytotoxic protein, which has extremely high anticancer effect in terms of biological activity and has extremely high research value. And dolastatin 10 (D10) is the most studied one and is the representative of dolastatin. [2-3] D10 is a protein composed of 4 amino acids, which is formed by condensation of 4 amino acids dolavaline (Dov), valine, dolaisoleuine (Dil), dolaproine (Dap) and dolaphenie (Doe) as the carboxyl terminal. The yield of natural D-10 is extremely small, and the existing synthetic methods and routes cannot be produced on a large scale. The main reason is that the Dolaproine (Dap) with three chiral centers in D-10 cannot be efficiently stereoselectively synthesized....

Claims

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Application Information

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IPC IPC(8): C07F5/02
CPCC07F5/025
Inventor 黄保华刘晓栋戴建胡新礼
Owner SUZHOU IBIO TECH CO LTD
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