Method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of method

A technology of butyrolactone and hydrochloride, which is applied in the field of pesticide chemistry, can solve the problems of high price and long steps, and achieve the effects of reduced production cost, high yield, and simple operation and purification process

Inactive Publication Date: 2016-10-26
李建中
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] This route not only has long steps, but also uses the more expensive highly toxic methyl iodide in the reaction process.

Method used

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  • Method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of method
  • Method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of method
  • Method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] The preparation of embodiment 1 (S)-3-amino-γ-butyrolactone hydrochloride

[0028] Add 1L of water into the three-necked flask, add L-methionine (200g), chloroacetic acid (126.7g) and concentrated hydrochloric acid (112mL) in turn while stirring, and heat up to 100°C after the addition, and react for 6 hours. Cool to room temperature, and concentrate under reduced pressure to remove the solvent. Ethanol (200 mL) was added to the residue, the temperature was raised to reflux, and the mixture was stirred for 1 hour. Cool to room temperature, stir for 6 hours, and filter with suction to obtain 151.2 g of white solid ((S)-3-amino-γ-butyrolactone hydrochloride), yield: 82%.

Embodiment 2

[0030] Add 1L of water into the three-necked flask, add L-methionine (200g), bromoacetic acid (204.9g) and concentrated hydrochloric acid (112mL) sequentially under stirring, heat up to 100°C after addition, and react for 4 hours. Cool to room temperature, and concentrate under reduced pressure to remove the solvent. Isopropanol (200 mL) was added to the residue, the temperature was raised to reflux, and the mixture was stirred for 2 hours. Cool to room temperature, stir for 6 hours, and filter with suction to obtain 156.7 g of white solid ((S)-3-amino-γ-butyrolactone hydrochloride), yield: 85%.

Embodiment 3

[0032] Add 1L of water into the three-necked flask, add L-methionine (200g), chloroacetic acid (190g) and concentrated hydrochloric acid (134mL) in turn while stirring, and then raise the temperature to 100°C and react for 6 hours. Cool to room temperature, and concentrate under reduced pressure to remove the solvent. Ethanol (250 mL) was added to the residue, the temperature was raised to reflux, and the mixture was stirred for 1 hour. Cool to room temperature, stir for 10 hours, and filter with suction to obtain 156.7 g of white solid ((S)-3-amino-γ-butyrolactone hydrochloride), yield: 85%.

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Abstract

The invention relates and belongs to the field of pesticide chemistry, and in particular relates to a method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride, and application of the method. The method takes L-methionine, concentrated hydrochloric acid and chloroacetic acid or bromoacetic acid as raw materials, and the L-glufosinate-ammonium intermediate (S)-3-amino-gamma-butyrolactone hydrochloride is obtained by a one-pot reaction. The method is simple in operation process and purification process, and high in yield; after the method is adopted, the production cost of L-glufosinate-ammonium is remarkably lowered.

Description

technical field [0001] The invention belongs to the field of pesticide chemistry, and specifically relates to a method for synthesizing L-glufosinate-ammonium intermediate (S)-3-amino-γ-butyrolactone hydrochloride and its application. Background technique [0002] Glufosinate-ammonium is a new type of herbicide developed by Hearst (currently owned by Bayer) in the 1980s. It can be used in orchards, vineyards, and non-cultivated land to control annual and perennial dicotyledonous and gramineous weeds. It is currently the second largest genetically modified crop resistant to herbicides in the world after glyphosate. Mode of action and mechanism of glufosinate-ammonium: It is mainly absorbed by contact with green stems and leaves of plants, with limited systemic action and xylem conduction and no soil herbicidal activity. It has ammonium accumulative contact, inhibits the activity of glutamine synthetase in plants, resulting in blocked glutamine synthesis, disordered nitrogen ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/33C07F9/30
CPCC07D307/33C07F9/301
Inventor 李建中郭增山
Owner 李建中
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