Preparation method of L-glufosinate-ammonium

A technology of glufosinate-ammonium and chiral prosthetic group, applied in the field of organic chemistry, can solve the problems of waste water generation, strict growth environment, and influence on enzyme activity.

Inactive Publication Date: 2020-04-28
CHINA PHARM UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The biological resolution method needs to use the derived DL-glufosinate as the raw material, which involves the chemical racemization and cyclic resolution of the invalid enantiomer. Although the biological asymmetric synthesi

Method used

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  • Preparation method of L-glufosinate-ammonium
  • Preparation method of L-glufosinate-ammonium
  • Preparation method of L-glufosinate-ammonium

Examples

Experimental program
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Effect test

Embodiment 1

[0017] Example 1: In a 250ml there-necked flask equipped with a thermometer and mechanical stirring, add 4.0 grams of sodium hydroxide, add 100 ml of methanol, 10.0 grams of DL-glufosinate-ammonium, 12.0 grams of nickel chloride hexahydrate, and 22.7 grams of chiral prosthetic groups, Slowly raise the temperature to 60°C for reaction. After the reaction, 60ml of methanol is distilled off under reduced pressure, the solid sodium hydroxide is filtered out, and the filtrate continues to concentrate to form a red solid. Add 30ml of 3M hydrochloric acid to the red solid, react at 100 degrees Celsius for 3 hours, the red color disappears, filter to obtain the chiral prosthetic group, dry and weigh 22.4 grams, dehydrate the filtrate, add 20ml of absolute ethanol, let it stand for 2 hours, and precipitate glufosinate-ammonium hydrochloride. The filtrate was concentrated to obtain 11.5 g of nickel chloride hexahydrate. Glufosinate-ammonium hydrochloride was dissolved in methanol, ammon...

Embodiment 2

[0018] Example 2: In a 250ml there-necked flask equipped with a thermometer and mechanical stirring, add 5.6 grams of potassium hydroxide, add 100 ml of methanol, 10.0 grams of DL-glufosinate-ammonium, 12.0 grams of nickel chloride hexahydrate, and 22.7 grams of chiral prosthetic groups, Slowly raise the temperature to 60°C for reaction. After the reaction is completed, 60ml of methanol is distilled off under reduced pressure, the potassium hydroxide solid is filtered out, and the filtrate continues to concentrate to form a red solid. Add 30ml of 3M hydrochloric acid to the red solid, react at 100 degrees Celsius for 3 hours, the red color disappears, filter to obtain the chiral prosthetic group, dry and weigh 22.2 grams, dehydrate the filtrate, add 20ml of absolute ethanol, let it stand for 2 hours, and precipitate glufosinate-ammonium hydrochloride. The filtrate was concentrated to obtain 11.6 g of nickel chloride hexahydrate. Dissolve glufosinate-ammonium hydrochloride in m...

Embodiment 3

[0019] Example 3: In a 250ml three-necked flask equipped with a thermometer and mechanical stirring, add 13.8 grams of potassium carbonate, 100 ml of acetonitrile, 10 grams of DL-glufosinate-ammonium, 13.1 grams of nickel sulfate hexahydrate, and 22.7 grams of chiral prosthetic groups, and slowly heat up Reaction at 60°C. After the reaction, 70ml of acetonitrile was distilled off under reduced pressure, potassium carbonate solid was filtered out, and the filtrate continued to concentrate to obtain a red solid. Add 20ml of 3M sulfuric acid to the red solid, react at 100 degrees Celsius for 3 hours, the red color disappears, filter to obtain the chiral prosthetic group, dry and weigh 22.2 grams, dehydrate the filtrate, add 20ml of absolute ethanol, let it stand for 2 hours, and precipitate glufosinate-ammonium hydrochloride. The filtrate was concentrated to obtain 12.8 g of nickel sulfate hexahydrate. Glufosinate-ammonium hydrochloride was dissolved in methanol, ammonia gas was ...

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Abstract

The invention discloses a preparation method of L-glufosinate-ammonium, and the method comprises the following steps: by using DL-glufosinate-ammonium as a starting raw material, complexing the DL-glufosinate-ammonium with a chiral auxiliary group and metal ions under the action of an inorganic alkali to form a coordination compound, and inversing the configuration of D-glufosinate-ammonium in theprocess to generate the L-glufosinate-ammonium. And by hydrolyzing the coordination compound, the L-glufosinate-ammonium is obtained, and meanwhile the chiral auxiliary group and the metal salt are recovered. The method is simple in process route, high in yield, low in cost and suitable for industrial production of the L-glufosinate-ammonium.

Description

Technical field: [0001] The invention relates to a preparation method of L-glufosinate-ammonium, belonging to the field of organic chemistry. Background technique: [0002] Glufosinate-ammonium, also known as glufosinate, has a chemical structure of 4-[hydroxy(methyl)phosphono]-DL-homoalanine. Hoechst developed it into a non-selective herbicide with high efficiency, broad spectrum and low toxicity. Glufosinate-ammonium, as a herbicide, has a remarkable weed-killing effect. Glufosinate-ammonium is very similar to glutamic acid in molecular structure, so it can reversibly bind to the active site of glutamine synthetase, thereby inhibiting the glutamine synthesis pathway in plants and eventually leading to plant death. Glufosinate-ammonium has two different enantiomers, but only L-glufosinate-ammonium has phytotoxicity, so the herbicidal activity of L-glufosinate-ammonium is twice that of the racemic mixture. [0003] At present, the production process of DL-glufosinate at h...

Claims

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Application Information

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IPC IPC(8): C07F9/30
CPCC07F9/301
Inventor 王志坚张大永
Owner CHINA PHARM UNIV
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