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Method for preparing levetiracetam intermediate 2-aminobutyric acid

A technology for aminobutyric acid and intermediates, which is applied in the field of preparation of levetiracetam intermediates, can solve the problem that the S-2-aminobutyramide process route has no literature reports, etc., to prevent polychlorinated products and prevent reactions Faster, less by-product effects

Active Publication Date: 2015-07-22
ZHEJIANG CHANGMING PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Taking butyric acid as the starting material first synthesizes 2-aminobutyric acid according to the inventive method, and then further synthesizes the operational route of S-2-aminobutyramide. There is no bibliographical information at present

Method used

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  • Method for preparing levetiracetam intermediate 2-aminobutyric acid
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  • Method for preparing levetiracetam intermediate 2-aminobutyric acid

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Experimental program
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Effect test

Embodiment 1

[0043]Take butyric acid (120.00g, 1.36mol) and BTC (12.11g, 0.04mol) to form a butyric acid reaction solution with a substance ratio of 1:0.03, and send the butyric acid reaction solution to the first pipeline through a liquid delivery pump chemical reactor (20 meters in length and 8 mm in inner diameter), and at the same time, chlorine gas is introduced into another branch of the first pipeline chemical reactor, and the flow rate in the tube is controlled so that the butyric acid and chlorine gas in the butyric acid reaction solution introduced The ratio of the amount is 1:1.5, the reactor is closed, and the reaction is carried out at a temperature of 110° C. for 10 h. After the reaction, the outflowing reaction liquid enters the rectification reactor, and the fraction at about 90°C (12mmHg) is collected by distillation to obtain 156.67g of 2-chlorobutyric acid, with a yield of 94.0% and a purity of 96.0%. 1 H NMR (DMSO, 500MHz): δ4.43-4.40 (m, 1H), 2.01-1.92 (m, 1H), 1.90-1....

Embodiment 2

[0046] Take butyric acid (120.00g, 1.36mol) and butyric anhydride (6.33g, 0.04mol) to form a butyric acid reaction solution with a substance ratio of 1:0.03, and send the butyric acid reaction solution to the first Pipelined reactor (20 meters in length, 8 millimeters in pipe inner diameter), slowly feed chlorine gas into another branch of the first piped reactor at the same time, control the flow rate in the pipe so that butyric acid and The molar ratio of chlorine gas to substance is 1:1.5, and the reactor is sealed and reacted at a temperature of 110°C for 10 hours. After the reaction, the outflowing reaction liquid enters the rectification reactor, and the fraction at about 90°C (12mmHg) is collected by distillation to obtain 141.67g of 2-chlorobutyric acid, with a yield of 85.0% and a purity of 88.0%.

[0047] Take the above obtained 2-chlorobutyric acid (141.67g, 1.16mol) and ammonium chloride (92.77g, 1.73mol) to form a 2-chlorobutyric acid reaction solution with a mass...

Embodiment 3

[0049] Take butyric acid (120.00g, 1.36mol) and thionyl chloride (4.76g, 0.04mol) to form a butyric acid reaction solution with a substance ratio of 1:0.03, and send the butyric acid reaction solution to In the first pipelined reactor (20 meters in length and 8 mm in inner diameter of the tube), chlorine gas is slowly introduced into another branch of the first pipelined reactor at the same time, and the flow rate is controlled so that the butyric acid in the butyric acid reaction solution introduced The molar ratio of the substance to the chlorine gas is 1:1.5, the reactor is closed, and the reaction is carried out at a temperature of 110°C for 10h. After the reaction, the outflowing reaction liquid enters the rectification reactor, and the fraction at about 90°C (12mmHg) is collected by distillation to obtain 146.67g of 2-chlorobutyric acid, with a yield of 88.0% and a purity of 94.0%.

[0050] Take the above obtained 2-chlorobutyric acid (146.67g, 1.20mol) and ammonium chlo...

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Abstract

The invention discloses a method for preparing a levetiracetam intermediate 2-aminobutyric acid shown in a formula (III) in the specification. The method comprises the following steps of reacting a butyric acid raw material with chlorine in the presence of a catalyst in a first pipeline reactor to obtain 2-chlorobutyric acid shown in a formula (II) in the specification; performing ammonification reaction on 2-chlorobutyric acid in the presence of ammonium chloride and sodium hydroxide aqueous solution in a second pipeline reactor to obtain 2-aminobutyric acid shown in the formula (III) in the specification. The method is high in atom economy, convenient to operate and suitable for industrial production, and few byproducts are produced.

Description

(1) Technical field [0001] The invention relates to a preparation method of a levetiracetam intermediate, in particular to a method for obtaining 2-aminobutyric acid through chlorination and amination reactions of butyric acid. (2) Background technology [0002] Optically active amino acids and their derivatives, amides, are important intermediates for the industrial production of various physiologically active substances, such as medicines and pesticides. 2-amino-butyric acid (2-amino-butyric acid) is a natural amino acid that inhibits the transmission of human nerve information. It is also an important chemical raw material and pharmaceutical intermediate, and is widely used in the synthesis of levetiracetam drugs. 2-aminobutyric acid of the present invention can be used for another key intermediate of synthesizing levetiracetam, and its chemical name is S-2-aminobutanamide, and structural formula is as follows: [0003] [0004] The common synthetic techniques for pre...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C227/04
Inventor 夏建胜李坚军周章兴钱刚陈德响
Owner ZHEJIANG CHANGMING PHARMA
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