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Deprotection agent for halofuginone intermediate and application of deprotection agent

A technology of deprotection agent and halofuginone, applied in the field of deprotection agent of halofuginone intermediates, can solve the problems of low yield, impure product, many side reactions, etc., and achieves high yield, short reaction time, high yield and the like. rate effect

Active Publication Date: 2022-05-06
CHONGQING UNIV OF EDUCATION
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0013] Aiming at the deficiencies in the prior art, the present invention provides a deprotecting agent for hemosanone intermediate and its application, which solves the many side reactions, impure product and low yield in the prior art The problem

Method used

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  • Deprotection agent for halofuginone intermediate and application of deprotection agent
  • Deprotection agent for halofuginone intermediate and application of deprotection agent
  • Deprotection agent for halofuginone intermediate and application of deprotection agent

Examples

Experimental program
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Effect test

Embodiment 1

[0034] Embodiment 1 hemosanone intermediate deprotection reaction

[0035] In a clean 100ml three-necked flask, add 2.65g of a hemosanone intermediate (represented by SD-5, whose structural formula is shown in formula I), 35ml of methanol, 17.5ml of purified water, 1.75ml of glacial acetic acid and zinc / iron powder (mass ratio 1:1) 0.8g, adjust the pH value to 2.0, raise the temperature to 70°C, reflux for 5h, and stop the reaction. Filtrate with suction, concentrate the filtrate, transfer the concentrate to a separatory funnel, add 20ml of chloroform, take the water layer, extract the chloroform layer with 1M hydrochloric acid (10ml-20ml) x 3, combine the water layers, adjust the pH to 8 with 3M NaOH, and the system precipitates White solid, filtered with suction, took the filter cake, added 30ml of chloroform for ultrasonic beating, filtered, concentrated under reduced pressure to obtain an oil, then added 5ml of ethyl acetate to crystallize, filtered with suction, and dri...

Embodiment 2

[0036] Embodiment 2 hemosanone intermediate deprotection reaction

[0037] In a clean 100ml three-neck flask, add SD-5 5g, methanol 30.49ml, purified water 18.30ml, glacial acetic acid 1.21ml and zinc / iron powder (5:1) 1.0g at T=30℃, and adjust the pH value to 2.5, heat up to 75°C, reflux for 3 hours, continue stirring for 45 minutes, and stop the reaction. Filtrate with suction, concentrate the filtrate, transfer the concentrate to a separatory funnel, add 20ml of chloroform, take the water layer, extract the chloroform layer with 1M hydrochloric acid (10ml-20ml) x 3, combine the water layers, adjust the pH to 8 with 3M NaOH, and the system precipitates White solid, filtered with suction, took the filter cake, added 30ml of chloroform for ultrasonic beating, filtered, concentrated under reduced pressure to obtain an oil, then added 5ml of ethyl acetate for crystallization, filtered with suction, and dried to obtain 1.60g of the product, HPLC purity 97.5% , yield 86.2%.

Embodiment 3

[0038] Embodiment 3 hemosanone intermediate deprotection reaction

[0039] Add 2g of SD-5, 64ml of methanol, 32ml of purified water, 4ml of glacial acetic acid and 1.0g of zinc / iron powder (1:5) in a clean 100ml three-neck flask at T = 25°C, adjust the pH value to 3.0, and raise the temperature To 72°C, reflux for 4 hours, continue stirring for 45 minutes, and stop the reaction. Filtrate with suction, concentrate the filtrate, transfer the concentrate to a separatory funnel, add 20ml of chloroform, take the water layer, extract the chloroform layer with 1M hydrochloric acid (10ml-20ml) x 3, combine the water layers, adjust the pH to 8 with 3M NaOH, and the system precipitates White solid, filtered with suction, took the filter cake, added 30ml of chloroform for ultrasonic beating, filtered, concentrated under reduced pressure to obtain an oil, then added 5ml of ethyl acetate for crystallization, filtered with suction, and dried to obtain 1.66g of the product, HPLC purity 97.1%...

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Abstract

The invention provides a deprotection agent for a halofuginone intermediate and application of the deprotection agent. The deprotection agent comprises a metal reducing agent and a mixed solvent, the metal reducing agent comprises zinc powder and iron powder, and the mixed solvent comprises methanol, glacial acetic acid and water. The method for deprotecting the halofuginone intermediate comprises the following steps: 1) dissolving the halofuginone intermediate in a mixed solvent; and 2) adding a metal reducing agent, and performing reflux reaction. The deprotection agent disclosed by the invention can be selectively and efficiently removed under a highly specific condition, other parts of molecules are not influenced, and the product is high in purity, high in yield and high in efficiency.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a deprotecting agent used for a hemosanone intermediate and an application thereof. Background technique [0002] Halofuginone (Hal), the chemical name is 7-bromo-6-chloro-3-[3-(3-hydroxy-2-piperidinyl)-2-oxopropyl(acetonyl)]-4(3H )-quinazolone hydrobromic acid is a kind of quinazolinone alkaloid, which is a derivative of the Chinese medicine Radix Changshan extract. Its chemical structure is shown in formula III: [0003] [0004] At present, the commercial hemosanone is mainly the hydrobromide formula of hemosanone, and the hydrobromide is a white or off-white crystalline powder, which is odorless, tasteless, and has good stability. Currently, it is mainly used for domesticating animals such as poultry and livestock. Anti-coccidiosis, anti-malarial prevention and treatment, 3ppm concentration in the feed can effectively control 6 kinds of Eimeria coccidiosis. Re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D405/06C07D401/06
CPCC07D405/06C07D401/06Y02P20/55
Inventor 任彦荣李园园杨怡萌
Owner CHONGQING UNIV OF EDUCATION