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Method for catalytically synthesizing L-cis-1,2-epoxypropylphosphonic acid-D-alpha-phenylethylamine by using phosphotungstic heteropoly acid phase transfer catalyst

A phase transfer catalyst, the technology of levophosphorus dexamine salt, which is applied in chemical instruments and methods, preparation of amino compounds from amines, compounds of elements of Group 5/15 of the periodic table, etc., can solve the problem that the catalyst cannot be recycled and restricts the production cost of products and other problems, to achieve the effect of high recovery rate, high catalytic activity and lower production cost

Inactive Publication Date: 2016-02-10
DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The purpose of the present invention is to provide a kind of preparation method of left phosphorus right ammonium salt, to overcome the defect that the catalyst can not be recycled to restrict the production cost of the product in the synthetic method of the prior art

Method used

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  • Method for catalytically synthesizing L-cis-1,2-epoxypropylphosphonic acid-D-alpha-phenylethylamine by using phosphotungstic heteropoly acid phase transfer catalyst
  • Method for catalytically synthesizing L-cis-1,2-epoxypropylphosphonic acid-D-alpha-phenylethylamine by using phosphotungstic heteropoly acid phase transfer catalyst
  • Method for catalytically synthesizing L-cis-1,2-epoxypropylphosphonic acid-D-alpha-phenylethylamine by using phosphotungstic heteropoly acid phase transfer catalyst

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0009] In a three-neck flask equipped with a magnetic stirrer and a thermometer, add 3.0 g of crude cis-acrylphosphonic acid and 10 mL of ethanol with a mass concentration of 95%, and stir to dissolve at room temperature. Control the temperature in the water bath to 30-40°C, slowly add α-phenylethylamine dropwise, adjust the pH=5.5-6.0, and continue stirring for 5 minutes after dropping. Add 0.1714g of catalyst wet product (containing about 30wt% ethanol) and 0.03g of EDTA, heat to 40-50°C, slowly add 3.065g of hydrogen peroxide solution with a mass concentration of 30%, after the dropwise addition, keep the temperature at 50°C for reaction, 1 HNMR detection reaction. After the reaction is completed, cool down to -5~-10°C, keep warm for 0.5h, filter with suction, wash the filter cake with ethanol at 0~-5°C, and refine it to obtain Zuo salt ( 1 HNMR confirmed the structure: (1R,2S)-(-)-cis-1,2-epoxypropyl phosphate-R-(+)-α-phenethylamine salt). The filtrate was raised to room...

Embodiment 2

[0013] In a three-neck flask equipped with a magnetic stirrer and a thermometer, add 3.0 g of crude cis-acrylphosphonic acid and 10 mL of ethanol with a mass concentration of 95%, and stir to dissolve at room temperature. Control the temperature in the water bath to 30-40°C, slowly add α-phenylethylamine dropwise, adjust the pH=5.5-6.0, and continue stirring for 5 minutes after dropping. Add 0.0857g catalyst wet product (containing about 30wt% ethanol) and 0.03g EDTA, heat to 40-50°C, slowly add 3.345g of hydrogen peroxide solution with a mass concentration of 30%, after the dropwise addition, keep the temperature at 50°C for reaction, 1 HNMR detection reaction. After the reaction is completed, cool down to -5~-10°C, keep warm for 0.5h, filter with suction, wash the filter cake with ethanol at 0~-5°C, and refine it to obtain Zuo salt ( 1 HNMR confirmed the structure: (1R,2S)-(-)-cis-1,2-epoxypropyl phosphate-R-(+)-α-phenethylamine salt). The filtrate was raised to room tempe...

Embodiment 3

[0018] In a three-neck flask equipped with a magnetic stirrer and a thermometer, add 3.0 g of crude cis-acrylphosphonic acid and 10 mL of ethanol with a mass concentration of 95%, and stir to dissolve at room temperature. Control the temperature in the water bath to 30-40°C, slowly add α-phenylethylamine dropwise, adjust the pH=5.5-6.0, and continue stirring for 5 minutes after dropping. Add 0.1714g of catalyst wet product (containing about 30wt% ethanol) and 0.03g of EDTA, heat to 40-50°C, slowly add 3.065g of hydrogen peroxide solution with a mass concentration of 30%, after the dropwise addition, keep the temperature at 50°C for reaction, 1 HNMR detection reaction. After the reaction is completed, cool down to -5~-10°C, keep warm for 0.5h, filter with suction, wash the filter cake with ethanol at 0~-5°C, and refine it to obtain Zuo salt ( 1 HNMR confirmed the structure: (1R,2S)-(-)-cis-1,2-epoxypropyl phosphate-R-(+)-α-phenethylamine salt). The filtrate was raised to room...

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Abstract

The invention relates to a method for catalytically synthesizing L-cis-1,2-epoxypropylphosphonic acid-D-alpha-phenylethylamine by using a phosphotungstic heteropoly acid phase transfer catalyst. By taking cis-1-propenylphosphonic acid, alpha-phenylethylamine and a hydrogen dioxide solution as raw materials, L-cis-1,2-epoxypropylphosphonic acid-D-alpha-phenylethylamine is catalytically synthesized by using the phosphotungstic heteropoly acid phase transfer catalyst in the presence of industrial ethanol and EDTA. After a product is separated, the pH of the filtrate is adjusted by using a solution A with certain concentration, so that the catalyst is fully separated out, and the catalyst is recycled and can be repeatedly used for three times; the recovery rate of the catalyst per time is relatively high. The method provided by the invention is low in production cost and less in emission, and meets the demand of current green chemistry and atom economy.

Description

technical field [0001] The invention relates to a preparation method of left phosphorus and right ammonium salt, in particular to a method for preparing left phosphorus and right ammonium salt by catalytic oxidation with phosphotungstic heteropolyacid phase transfer catalyst. Background technique [0002] Fosfomycin is a broad-spectrum antibacterial drug with low toxicity and side effects. It has a synergistic effect with most antibiotics. It is sensitive to Staphylococcus, Escherichia coli, Serratia, Proteus, etc., and can inhibit the synthesis of bacterial cell walls. It is a kind of fungicide during the breeding period and has a wide range of applications. In the industrial production process of fosfomycin, the epoxidation reaction of cis-acrylophosphate is one of the key steps in the chemical synthesis of fosfomycin by Glamkowski method. At present, homogeneous sodium tungstate is used as the epoxidation catalyst at home and abroad. The catalyst has high activity and ca...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/655C07C211/27C07C209/68
CPCY02P20/584
Inventor 史海赵许群王晓东张涛
Owner DALIAN INST OF CHEM PHYSICS CHINESE ACAD OF SCI
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