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Preparation method of aminohexenoic acid

A technology of aminohexenoic acid and alkenoic acid ester, which is applied in the preparation of carboxylate, the preparation of organic compounds, the preparation of cyanide reaction, etc., can solve the problems such as the inability to obtain high-purity 4-amino-5-hexenoic acid, Achieve the effect of strong industrial practicability and simple operation

Active Publication Date: 2020-01-21
WUHAN WUYAO SCI & TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] Yet above-mentioned method all can not obtain the 4-amino-5-hexenoic acid of high purity, in view of this, propose the present invention

Method used

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  • Preparation method of aminohexenoic acid
  • Preparation method of aminohexenoic acid
  • Preparation method of aminohexenoic acid

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Add 5L of 20% sodium ethoxide ethanol solution into the enamel reaction kettle, start stirring, and raise the temperature to 55°C; weigh 1kg of diethyl malonate, add it dropwise to the above enamel reaction kettle, add 0.4kg of hydroquinone; Take trans-1,4-dichloro-2-butene, the molar ratio of trans-1,4-dichloro-2-butene to diethyl malonate is 1:1, add it dropwise to the above enamel reaction In the kettle, the dropwise addition was completed in 1.5 to 2 hours; weigh 1L of 20% sodium ethoxide ethanol solution, and add it dropwise to the above-mentioned enamel reaction kettle, and the dropwise addition was completed in 1 to 1.5 hours; the temperature was raised to reflux, and the reaction was performed for 3 hours; the reaction was completed, and the heating was stopped. , cooling down; quenched with water; extracted twice with methyl tert-butyl ether whose volume was 3 times the mass of trans-1,4-dichloro-2-butene, combined the organic layers; Wash twice with sodium chl...

Embodiment 2

[0052] Add 5L of 20% sodium ethoxide ethanol solution into the enamel reaction kettle, start stirring, and raise the temperature to 60°C; weigh 1kg of diethyl malonate, add it dropwise to the above enamel reaction kettle, add 0.5kg of hydroquinone; Take trans-1,4-dichloro-2-butene, the molar ratio of trans-1,4-dichloro-2-butene to diethyl malonate is 1:1, add it dropwise to the above enamel reaction In the kettle, the dropwise addition was completed in 1.5 to 2 hours; weighed 1L of 20% sodium ethoxide ethanol solution, and added dropwise to the above-mentioned enamel reaction kettle, and the dropwise addition was completed in 1 to 1.5 hours; the temperature was raised to reflux, and the reaction was 3.5h; the reaction was completed, stop Heating, cooling down; quenching with water; extracting twice with methyl tert-butyl ether whose volume is 5 times the mass of trans-1,4-dichloro-2-butene, and combining the organic layers; The same amount of base ether was washed with water t...

Embodiment 3

[0059] The operation of preparing AX-4 crude product is the same as that in Example 1.

[0060] Dissolve 500g of triisopropylsilyl 4-aminohex-5-enoate in 8 times volume / mass of chloroform / methanol mixed solution, the volume ratio of chloroform to methanol is 1:7, heat up to 50-60°C, Add cyclohexane dropwise under stirring at a speed of 100rpm, the volume ratio of cyclohexane and chloroform / methanol mixed solution is 1:10, keep stirring for 30min after dropping, drop to 40°C at a speed of 13°C / min, and stir for 30min at a speed of 100rpm , stood still for 2h, and filtered to obtain 485g of purified triisopropylsilyl 4-aminohex-5-enoate, with an HPLC content of 99.01%.

[0061] Dissolve 400g of triisopropylsilyl 4-aminohex-5-enoate purified product in 2L methanol aqueous solution (concentration 50%), add 0.5L sodium hydroxide aqueous solution (concentration 30%), and heat up to 45 ℃, heat preservation reaction for 2 hours, distilled off the water under reduced pressure, and add...

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Abstract

The invention discloses a preparation method of aminohexenoic acid, which is characterized by comprising the following steps: with diethyl malonate and 1,4-dichloro-2-butene as raw materials, preparing 2-vinylcyclopropane-1,1-dicarboxylic acid diethyl ester; then carrying out a reaction on 2-vinylcyclopropane-1,1-dicarboxylic acid diethyl ester in the presence of ammonia and formamide to prepare 2-carbonyl-5-vinyl-pyrrolidine-3-amide; preparing a 4-amino-5-hexenoic acid crude product from the 2-carbonyl-5-vinyl-pyrrolidine-3-amide under an acidic condition; then preparing triisopropylsilyl-4-aminohexyl-5-alkenyl ester from 4-amino-5-hexenoic acid and triisopropylchlorosilane in the presence of triethylamine and ammonia; recrystallizing the triisopropylsilyl-4-aminohexyl-5-alkenyl ester inchloroform / methanol to obtain a purified product of the triisopropylsilyl-4-aminohexyl-5-alkenyl ester; wherein the volume ratio of chloroform to methanol is 1:7; and hydrolyzing the purified productof the triisopropylsilyl-4-aminohexyl-5-alkenyl ester under an alkaline condition to obtain the aminohexylenic acid.

Description

technical field [0001] The application belongs to the field of pharmacy, and in particular relates to a preparation method of vigabatrin. Background technique [0002] Vigabatrin is an antiepileptic drug, which is clinically used to treat epilepsy, especially partial seizures, where other antiepileptic drugs are ineffective. Its chemical name is 4-amino-5-hexenoic acid, and its molecular formula is C 6 h 11 NO 2 , with a molecular weight of 129.157, is an analogue of γ-aminobutyric acid (GABA), which can specifically bind to GABA aminotransferase and is irreversible, leading to an increase in the concentration of GABA in the brain, thereby exerting an antiepileptic effect. Vigabatrin is used as an adjuvant therapy in patients who do not respond to other antiepileptic drugs, especially in patients with partial seizures (mainly for the control of complex partial seizures), and in West syndrome ( infantile spasms). As an adjuvant drug, vigabatrin can obtain better curative...

Claims

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Application Information

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IPC IPC(8): C07C67/343C07C69/743C07D207/277C07C227/22C07C227/40C07C227/18C07C229/30C07F7/18
CPCC07C67/343C07D207/277C07C227/22C07C227/40C07C227/18C07F7/188C07C69/743C07C229/30
Inventor 黄赟杨波陈彦田俊峰朱毅郭亚兵刘祥
Owner WUHAN WUYAO SCI & TECH
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