Synthetic method for 2-(N-4-fluorobenzyl) methoxy-acetyl-amino methyl isobutyrate

A technology of methyl methoxyacetamidoisobutyrate and methyl fluorobenzylidene aminoacetate, which is applied in the field of organic chemical synthesis, can solve the problems of difficult electrocarboxylation, complicated preparation process, and poor stability, and achieves The effects of reducing air pollution, cheap and easy-to-obtain raw materials, and convenient operation

Inactive Publication Date: 2012-09-12
EAST CHINA NORMAL UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

So far, there have been no studies or reports on the electrocarboxylation of methyl 4-fluorobenzylidene aminoacetate containing a C=N activating group
Methyl 4-fluorobenzylidene aminoacetate is a benzene ring with a 4-position substituent on one side of the C=N group, which is a fluorine atom. It has poor stability and is easily decomposed when it meets water and acid. Therefore, the electrocarboxylation reaction of this compound It is generally difficult to carry out, the preparation process is complicated, and it is not easy to operate

Method used

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  • Synthetic method for 2-(N-4-fluorobenzyl) methoxy-acetyl-amino methyl isobutyrate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0016] a. Preparation of electrolyte

[0017] Mix 0.001mol (0.195g) methyl 4-fluorobenzylidene aminoacetate with 0.001mol (0.210g) tetraethylammonium bromide and 0.129mol (10 mL) N,N-dimethylformamide to form an electrolyte, Then put it into a one-compartment electrolytic cell with stainless steel as the cathode and magnesium rod as the anode, methyl 4-fluorobenzylidene aminoacetate, tetraethylammonium bromide and N,N-dimethylformamide are analytically pure, of which : Methyl 4-fluorobenzylidene aminoacetate is the substrate, N,N-dimethylformamide is the solvent after drying with 4? grade molecular sieves, and tetraethylammonium bromide is the supporting electrolyte.

[0018] b. Electrocarboxylation reaction

[0019] Under normal pressure, carbon dioxide is introduced into the electrolytic cell to saturation, and then at 2.9mA / cm 2 The electrocarboxylation reaction was carried out at a constant current density with a flow rate of 193C and a reaction temperature of 25°C.

[...

Embodiment 2

[0025] a. Preparation of electrolyte

[0026] Mix 0.001mol (0.195g) methyl 4-fluorobenzylidene aminoacetate with 0.001mol (0.257g) tetraethylammonium iodide and 0.129mol (10 mL) N,N-dimethylformamide to form an electrolyte, Then put it into a one-chamber electrolytic cell with stainless steel as the cathode and magnesium rod as the anode, methyl 4-fluorobenzylidene aminoacetate, tetraethylammonium iodide and N,N-dimethylformamide are analytically pure, of which : Methyl 4-fluorobenzylidene aminoacetate is the substrate, N,N-dimethylformamide is the solvent after drying with 4? grade molecular sieves, and tetraethylammonium iodide is the supporting electrolyte.

[0027] b. Electrocarboxylation reaction

[0028] Under normal pressure, carbon dioxide is introduced into the electrolytic cell to saturation, and then at 2.9mA / cm 2 The electrocarboxylation reaction was carried out at a constant current density with a flow rate of 193C and a reaction temperature of 25°C.

[0029] c...

Embodiment 3

[0034] a. Preparation of electrolyte

[0035] Mix 0.001mol (0.195g) methyl 4-fluorobenzylidene aminoacetate with 0.001mol (0.165g) tetraethylammonium chloride and 0.129mol (10 mL) N,N-dimethylformamide to form an electrolyte, Then put it into a one-chamber electrolytic cell with stainless steel as the cathode and magnesium rod as the anode, methyl 4-fluorobenzylidene aminoacetate, tetraethylammonium chloride and N,N-dimethylformamide are analytically pure, of which : Methyl 4-fluorobenzylidene aminoacetate is the substrate, N,N-dimethylformamide is the solvent after drying with 4? grade molecular sieves, and tetraethylammonium chloride is the supporting electrolyte.

[0036] b. Electrocarboxylation reaction

[0037] Under normal pressure, carbon dioxide is introduced into the electrolytic cell to saturation, and then at 2.9mA / cm 2 The electrocarboxylation reaction was carried out at a constant current density with a flow rate of 193C and a reaction temperature of 22°C.

[0...

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Abstract

The invention discloses a synthetic method for 2-(N-4-fluorobenzyl) methoxy-acetyl-amino methyl isobutyrate. The synthetic method is characterized in that 4-fluorine benzal aminoacetic acid methyl ester, N, N-dimethyl formamide, tetraethyl ammonium bromide, tetraethyl ammonium iodide and tetraethyl ammonium chloride or tetrabutyl ammonium bromide are mixed to form an electrolyte, the electrolyte is electrolyzed by using continuous currents after carbon dioxide is saturated under an ordinary pressure, and an electrolyte is purified after being esterified to obtain the 2-(N-4-fluorobenzyl) methoxy-acetyl-amino methyl isobutyrate. Compared with the prior art, the synthetic method has the advantages that the method is simple, the raw materials are low in cost and easily obtained, the cost is low, and the carbon dioxide generated due to the greenhouse effect is effectively used, thereby greatly reducing the air pollution and opening up a new approach for the research of a green synthetic N-replaced a-amino acid derivative; and the synthetic method has very good application prospect and is a process route with the industrial synthetic value.

Description

technical field [0001] The invention relates to the technical field of organic chemical synthesis, in particular to a synthesis method of methyl 2-(N-4-fluorobenzyl)methoxyacetamido isobutyrate reported for the first time. Background technique [0002] In recent years, various organic compounds centered on the activation and fixation of carbon dioxide by electrochemical methods, including electrocarboxylation reactions containing activated groups such as C-X, C=C, and C=O, have attracted more and more attention. However, regarding C= However, there are few reports on the electrocarboxylation of N. Imine compound R with C=N activating group 1 C=NR 2 , when R 1 , R 2 When both are phenyl groups, imines are stable crystals; when R 1 , R 2 When one of them is a phenyl group, the stability of the imine decreases, and it is easy to decompose when it meets water and acid. When there is a substituent on the phenyl ring attached to the C=N side, it also has a great impact on th...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C271/22C07C269/00
Inventor 陆嘉星陈宝丽李瑞娜王欢肖艳屠卓莹丁彬彬
Owner EAST CHINA NORMAL UNIV
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