Method for preparing L-glufosinate-ammonium

A technology for glufosinate-ammonium and a compound is applied in the field of preparing L-glufosinate-ammonium, which can solve the problems of difficulty in realizing high-efficiency industrial production, expensive chiral resolution reagents, low industrial application value and the like, and achieves low price, short synthesis steps, The effect of less waste

Active Publication Date: 2020-09-15
LIER CHEM CO LTD +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Chemical synthesis of L-glufosinate-ammonium mainly includes chiral auxiliary agent induction method, racemate resolution method and asymmetric synthesis method, etc., but these methods face complex synthetic routes, low yield or / and chiral resolution reagents Expensive problem, it is difficult to achieve its efficient industrial production, or it is difficult to achieve greater industrial application value
Biological synthesis of L-glufosinate-ammonium mainly includes protease method, amino acid dehydrogenase method and transaminase method, etc. These methods often have defects such as low product optical purity, difficult separation or / and poor substrate tolerance, and their industrial application value relatively low

Method used

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  • Method for preparing L-glufosinate-ammonium

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0048] (1) Synthesis of compound 2

[0049]

[0050] Dissolve 50 g of L-homoserine (1) in 36% HCl solution (120 g), add 0.5 g of tetrabutylammonium bromide, react in a closed pressure-resistant reactor at 80° C. for 9 h, and cool naturally to room temperature. The reaction solution was detected by LC, and the reaction of the raw materials was complete. The reaction solution was directly suction-filtered and dried to obtain 50 g of light yellow solid compound 2 with a yield of 87%.

[0051] (2) Synthesis of compound 3

[0052]

[0053] Under a nitrogen atmosphere, 50 g of compound 2 (0.364 mol) and 150 mL of toluene were added to a 500 mL three-necked flask, and the temperature was raised to 40 ° C. At this temperature, 55 g (0.185 mol) of triphosgene in toluene (50 mL) was added dropwise. After the reaction was complete, the solvent was distilled off under reduced pressure, and then recrystallized from ethyl acetate to obtain compound 3 as a light yellow solid with a yi...

Embodiment 2

[0061]According to the method of Example 1, the reaction conditions of step (2) were changed, and the results are shown in Table 1 below. Wherein, the amount of triphosgene used is 0.5 equivalents, the amount of phosgene used is 1.5 equivalents, the amount of diphosgene used is 0.75 equivalents, and the amount of ethyl chloroformate is 1.5 equivalents.

[0062] Table 1

[0063] serial number Reagent solvent temperature reflex Compound 3 Yield 1 Triphosgene toluene 60℃ 61％ 2 Triphosgene toluene 110℃ 51％ 3 Triphosgene Tetrahydrofuran 40℃ 53％ 4 Triphosgene Tetrahydrofuran 60℃ 73％ 5 Triphosgene Dichloromethane 40℃ 51％ 6 Triphosgene 1,4-dioxane 40℃ 45％ 7 Triphosgene 1,4-dioxane 90℃ 48％ 8 Triphosgene MTBE 60℃ 59％ 9 Triphosgene 1,2-Dichloroethane 40℃ 41％ 10 Triphosgene ethyl acetate 40℃ 44％ 11 Triphosgene ethyl acetate 60℃ 62％ 12 Phosgene Tetrahydrofur...

Embodiment 3

[0066] (1) Synthesis of compound 2'

[0067]

[0068] Dissolve 50 g of L-homoserine (1) in 48% HBr in CH 3 In COOH solution (120g), react in a closed pressure-resistant reactor at 80°C for 6h, and after naturally cooling to room temperature, the reaction solution is detected by LC and LC-MS, and the raw materials are completely reacted. The reaction solution is directly suction filtered and dried to obtain 72g of brown yellow solid compound 2', yield 95%.

[0069] (2) Synthesis of compound 3'

[0070]

[0071] Under a nitrogen atmosphere, 50g of compound 2' and 150mL of tetrahydrofuran were added to a 500mL three-necked flask, and the temperature was raised to 60°C. At this temperature, 122g of triphosgene in THF (100mL) was added dropwise. After the solvent was distilled off under pressure, it was recrystallized from ethyl acetate to obtain 36 g of a light yellow solid with a yield of 73%.

[0072] (6) Synthesis of compound 4

[0073]

[0074] Under a nitrogen at...

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Abstract

The invention relates to a method for preparing L-glufosinate-ammonium. According to the method, cheap and easily available L-homoserine is used as an initial raw material, L-glufosinate-ammonium witha high ee value is prepared through a three-step reaction, chiral catalysis is not needed, the cost is low, and the method has a potential industrial application value.

Description

technical field [0001] The invention relates to a method for preparing L-glufosinate-ammonium. Background technique [0002] Glufosinate-ammonium is a broad-spectrum organophosphate contact herbicide successfully developed by Hearst in the 1980s. Glufosinate-ammonium is a glutamine synthesis inhibitor, and its systemic effect is not strong. Glyphosate kills roots differently. Glufosinate-ammonium kills leaves first, and then conducts transpiration in plant xylem through plant transpiration. Its quick-acting performance is between paraquat and glyphosate, and it is a non-selective contact herbicide. Glufosinate-ammonium includes L-glufosinate-ammonium and racemic DL-type glufosinate-ammonium, wherein the herbicidal activity of L-glufosinate-ammonium is twice that of racemic DL-type glufosinate-ammonium. Glufosinate-ammonium preparations currently on the market are generally racemic DL-type glufosinate-ammonium. If glufosinate-ammonium products can be used in the form of pure...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30C07D263/44
CPCC07F9/301C07D263/44C07B2200/07
Inventor 刘永江周磊曾伟刘俊强左翔程柯
Owner LIER CHEM CO LTD
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