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A kind of synthetic method of 3+2 ring closure

A synthetic method and technology of synthetic route, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of low selectivity, increased cost, low yield, etc., to shorten the reaction steps and reduce the three wastes. The effect of reducing emissions and simplifying the production process

Active Publication Date: 2020-11-27
苏州正济医药研究有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Due to the low selectivity of the reaction, the yield is very low, which increases the cost of industrialization and is difficult to purify

Method used

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  • A kind of synthetic method of 3+2 ring closure
  • A kind of synthetic method of 3+2 ring closure
  • A kind of synthetic method of 3+2 ring closure

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0022]

[0023] Add (-)-wens lactone (1mmol) to a 250ml three-necked flask, add triethylamine (3mmmol), after stirring well, add the toluene solution (2mmol) of the newly prepared chloroxime intermediate, and stir the reaction solution at room temperature , add water after the reaction is over, separate layers, take the toluene phase, wash the toluene phase twice with water, and let it stand for later use.

[0024]

[0025] Add the toluene solution containing compound I in the previous step into a 250ml three-necked flask, add nickel chloride hexahydrate (0.5mmol), dissolve with methanol, and cool to 0-5°C. Take another beaker, add sodium hydroxide (0.02mmol) and sodium borohydride (1.5mmol), dissolve in methanol and slowly drop into the three-necked flask, after the drop is complete, stir and react at room temperature for 12 hours. Samples were taken and the results analyzed by HPLC. After treatment, add ammonia water to quench the reaction, heat the layers at 40-50°C,...

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PUM

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Abstract

The invention discloses a synthesis method of a 3+2 closed ring. According to the method, chiral induction is enhanced under the spatial steric effect of bridge ring molecules, so that a ring closingreaction has efficient spatial selectivity. The method is applied to synthesis of peramivir and has the characteristics that the synthesis route is short, the stereoselectivity is high and the operation procedure is convenient.

Description

technical field [0001] The invention relates to the technical field of drug synthesis, in particular, the invention relates to a synthesis method of 3+2 ring closure. Background technique [0002] The antiviral drug Peramivir (Peramivir) was developed by American Biocrystal Pharmaceutical Co., Ltd. It is another new type of neuraminidase (NA) following the successful research and development of zanamivir and oseltamivir and its launch in 1999. ) Inhibitor anti-influenza virus drugs, used for the treatment and prevention of influenza A and B in adults and children. [0003] The chemical name of peramivir is (1S, 2S, 3R, 4R, 1'S)-(-)-3-[(1'-acetylamino-2'-ethyl)butyl]-4-[[(aminosubstance Amino)methyl]amino]-2-hydroxycyclopentane-1-carboxylic acid trihydrate, the chemical structural formula is as follows: [0004] [0005] At present, the patents related to the synthesis method of peramivir are CN1282316, CN1358170, CN1367776 and J.Med.Chem.2001, 44, 4379-4392, etc., using...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C277/08C07C279/16
CPCC07C231/12C07C277/08C07C2601/08C07D209/52C07C279/16C07C233/47
Inventor 葛敏李亮胡春晨王怀秋付明伟李令超
Owner 苏州正济医药研究有限公司
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