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Synthetic method of L-glufosinate intermediate

A synthesis method and glufosinate-ammonium technology are applied in the field of synthesis of L-glufosinate-ammonium intermediates, which can solve the problems of increasing the total cost of the process, high process risk, complicated process operation, etc., and achieve improved safety, reaction rate, The effect of reducing costs and avoiding racemization problems

Pending Publication Date: 2019-06-21
LIER CHEM CO LTD +1
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Problems solved by technology

[0003] Formula VI is an important intermediate for synthesizing L-glufosinate-ammonium. CN106083922A discloses a preparation method of refined glufosinate-ammonium, specifically disclosing the formula VI under the action of catalyst zinc bromide, boron trifluoride ether or lanthanum trichloride. The preparation method of VI (R 2 for-CO-OCH 2 CH 3 , R 3 with R 4 Both are ethyl), which used a large excess of diethyl methylphosphonite during the preparation of formula VI, which has the following disadvantages: (1) diethyl methylphosphonite burns in air at a high temperature, and the large amount of use results in The potential risk of the process is high; (2) a large amount of diethyl methylphosphonite needs to be recycled and reused, and the process operation is loaded down with trivial details; (3) the loss in the recovery process of diethyl methylphosphonite is large, increasing the process total cost

Method used

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  • Synthetic method of L-glufosinate intermediate
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  • Synthetic method of L-glufosinate intermediate

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preparation example Construction

[0020] Concrete, the synthetic method of L-glufosinate-ammonium intermediate shown in formula II comprises the following steps:

[0021]

[0022] Under the protective gas atmosphere, react the compound of formula I with diethyl methyl phosphinate in the presence of a catalyst to obtain the L-glufosinate-ammonium intermediate shown in formula II; the catalyst is MgBr 2 +PEG-400, LiBr+PEG-400, KCl+PEG-400, MgBr 2 +TBAB, MgCl 2 , MgBr 2 , TMSBr+TBAB, LaCl 3 +TBAB or CaCl 2 .

[0023] The inventor of the present invention has carried out a large amount of screenings to catalyst, finds that by adding MgBr 2 +PEG-400, LiBr+PEG-400, KCl+PEG-400, MgBr 2 +TBAB, MgCl 2 , MgBr 2 , TMSBr+TBAB, LaCl 3 +TBAB or CaCl 2 The consumption of diethyl methylphosphonite can be greatly reduced, and the safety and reaction rate of the process are improved. At the same time in the catalyst MgBr 2 +PEG-400, LiBr+PEG-400, KCl+PEG-400, MgBr 2 +TBAB, MgCl 2 Or under the action of MgBr, th...

Embodiment 1

[0041] In a 250mL four-necked flask, 4.88g of the compound of formula I (1eq), 3.51g of diethyl methylphosphonite (1.2eq), 0.16g of PEG-400 (0.02eq) and 0.147g of MgBr 2 (0.04eq), then replace the system with nitrogen three times, then heat to 120°C for 17 hours, after the reaction, the reaction system is down to room temperature, and the reaction situation is detected by sampling. The ee value of the compound of formula II is 99.0%, and the absolute yield is 79.3%. .

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Abstract

The invention provides a synthetic method of L-glufosinate intermediate shown as a formula II and belongs to the technical field of organic synthesis. The synthetic method comprises the step: under aprotective gas atmosphere, reacting a compound in a formula I with diethyl methyl phosphonate in the presence of a catalyst to obtain an intermediate shown as the formula II; the catalyst is MgBr2+PEG-400, LiBr+PEG-400, KCl+PEG-400, MgBr2+TBAB, MgCl2,MgBr2, TMSBr+TBAB, LaCl3+TBAB or CaCl2. The synthetic method provided by the invention has the benefits that as the catalyst is added, the dosage ofthe diethyl methyl phosphonate is reduced, and the process safety and the reaction rate are improved; meanwhile, the problem of reaction racemization can be solved, so that the ee value of a product is improved, the post-processing operation is simplified, and the process cost is reduced, therefore, the industrial application is more easy to perform.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a synthesis method of an L-glufosinate-ammonium intermediate. Background technique [0002] Glufosinate is a highly efficient, broad-spectrum, low-toxic, non-selective (killing) organophosphorus herbicide developed by Hearst in the 1980s. It can be used to control annual and perennial dicotyledonous and gramineous weeds. Glufosinate-ammonium has two enantiomers of L-type and D-type. L-type glufosinate-ammonium is the essence of glufosinate-ammonium, and its herbicidal activity is twice that of racemic DL-type glufosinate-ammonium. [0003] Formula VI is an important intermediate for synthesizing L-glufosinate-ammonium. CN106083922A discloses a preparation method of refined glufosinate-ammonium, specifically disclosing the formula VI under the action of catalyst zinc bromide, boron trifluoride ether or lanthanum trichloride. The preparation method of VI (R ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/30
Inventor 李世洪程柯左翔
Owner LIER CHEM CO LTD
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