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The synthetic method of kainic acid

A synthesis method and technology of kainic acid are applied in the field of synthesis of natural product kainic acid, and achieve the effects of simple operation process, low price and short reaction steps

Inactive Publication Date: 2017-10-20
SHAANXI NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The technical problem to be solved by the present invention is to overcome the problems existing in the existing kainic acid synthesis method, and to provide a method for synthesizing kainic acid with low raw material price, short reaction steps, simple and convenient operation process and high total product yield

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  • The synthetic method of kainic acid
  • The synthetic method of kainic acid
  • The synthetic method of kainic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0020] 1. Add 1.37g (59.6mmol) sodium metal into 120mL dry absolute ethanol, stir at room temperature for 2 hours to completely dissolve the sodium metal, and obtain a 0.5mol / L sodium ethoxide solution. Add 5.6g (23.8mmol) (S)-5-oxo-tetrahydrofuran-3-carbamate benzyl ester into the flask, stir at room temperature for 3 hours, add 60mL 1mol / L hydrochloric acid aqueous solution to quench the reaction, and use 100mL ethyl acetate Extracted 3 times, combined the organic phases, dried with anhydrous sodium sulfate, filtered, concentrated by rotary evaporator, and purified by column chromatography (the eluent was a mixture of petroleum ether and ethyl acetate with a volume ratio of 3:1) , to obtain 4.0 g of white solid compound 1 with a yield of 97%.

[0021] 2. Add 277mg (6.93mmol) of sodium hydride and 200mL of dry N,N-dimethylformamide into the reaction flask, and cool to -40°C under the protection of argon; dissolve 1.0g (5.77mmol) of compound 1 In 50mL of dry N,N-dimethylforma...

Embodiment 2

[0027] In step 2 of Example 1, 15 mg (0.3753 mmol) of sodium hydride and 2 mL of dry N,N-dimethylformamide were added to the reaction flask, and cooled to -40°C under the protection of argon; 50 mg ( 0.2887mmol) of compound 1 was dissolved in 1mL of dry N,N-dimethylformamide, slowly injected into the reaction vial with a syringe, and stirred at -40°C for 30 minutes; 58.2mg (0.3176mmol) of (E) -4-Bromo-1-chloro-2-methyl-2-butene was dissolved in 1 mL of dry N,N-dimethylformamide, injected slowly into the reaction vial with a syringe, and continued at -40 °C Stir for 30 minutes; warm the reaction to room temperature, add 480 mg (2.887 mmol) of dry potassium iodide and 0.3 mL (0.433 mmol) of lithium bistrimethylsilylamide, stir for 3 hours, and quench with saturated aqueous ammonium chloride solution after the reaction is complete reaction, extracted 3 times with 10mL ethyl acetate, combined the organic phases, successively washed with saturated sodium chloride (3 × 10mL), dried ...

Embodiment 3

[0029] In step 3 of Example 1, the 1.52g (4.04mmol) of pyridinium dichromate used was replaced with 1.33g (3.14mmol) of Dess-Martin oxidant, and the other steps of this step were the same as in Example 1 to obtain 308mg of colorless Transparent liquid compound 3, its yield is 85%. Other steps were the same as in Example 1 to obtain kainic acid with a total yield of 16.2%.

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Abstract

The invention discloses a synthetic method of kainic acid. The synthetic method comprises the steps of carrying out single-step series connection N-allylation-SN2' reaction on (S)-5-oxo-tetrahydrofuran-3-carbamic acid benzyl ester as a raw material to construct a kainic acid core framework-trans-2,3-cis-3,4-trans-trisubstituted pyrrolidine intermediate, reducing and oxidizing an ester group in the intermediate into an aldehyde group, carrying out Horner-Wordsworth-Emmons reaction and mercury ion accelerated methanol hydrolysis reaction to obtain the ester group added with a carbon atom, finally carrying out ester exchange, oxidization and hydrolysis, so as to obtain kainic acid. The synthetic method has the beneficial effects that the raw material cost is low, the reaction steps are short, the operation process is simple and convenient, the total yield of kainic acid is high, the synthetic cost of kainic acid can be greatly lowered, and the industrial production of kainic acid is hopefully realized.

Description

technical field [0001] The invention belongs to the technical field of synthesis of natural products, and in particular relates to a synthesis method of natural product kainic acid. Background technique [0002] Epilepsy is a common disease of the nervous system, and its pathogenesis is not very clear at present, so its mechanism research has been widely valued by the scientific community. Kainic acid (CAS: 58002-62-3) is an acidic amino acid with two carboxyl groups extracted from Japanese red seaweed. It is a structural analog of glutamic acid, and it has a high selective damage. Intracerebral targeted injection or systemic administration of convulsive doses of kainic acid can induce experimental epileptic seizures in animals. This model is highly similar to the clinical manifestations and neuropathological changes of human temporal lobe epilepsy, and is recognized by the academic community as relatively An ideal animal model of human temporal lobe epilepsy, in addition,...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D207/16
CPCC07D207/16
Inventor 杨俊石宏伟石珊李建龙黄治炎
Owner SHAANXI NORMAL UNIV
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