A kind of synthetic method of α-aryl substituted glycine ester derivatives

A synthesis method and technology of glycinate, applied in the direction of chemical instruments and methods, preparation of organic compounds, cyanide reaction preparation, etc., can solve the problems of large amount of oxidant, metal residues, application restrictions, etc., and achieve high product yield and easy operation Convenience and good reaction selectivity

Active Publication Date: 2021-06-25
ZHEJIANG UNIV OF TECH
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] The above synthetic methods for the preparation of α-aryl substituted glycine ester derivatives are mostly realized through the catalytic system of metal copper combined with oxidant, which has the problems of large amount of oxidant and metal residue, which limits the application of this catalytic system.

Method used

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  • A kind of synthetic method of α-aryl substituted glycine ester derivatives
  • A kind of synthetic method of α-aryl substituted glycine ester derivatives

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] 2-(p-Toluidine) ethyl acetate (0.5 mmol, 96.6 mg), N - Add methylaniline (1.0 mmol, 107 mg) and methylene blue (0.025 mmol, 8 mg) into a 25 mL two-necked flask, then add tetrahydrofuran (5 mL) as a solvent, stir, and irradiate with blue light from a 3W LED lamp , reacted at a temperature of 40°C in an air atmosphere for 8 hours. After the reaction was completed, water and methylene chloride were added to the reaction system, and the layers were extracted and separated into an aqueous layer and an organic layer. Anhydrous sodium sulfate was added to the organic layer for drying. The dried organic layer was concentrated by distillation under reduced pressure to obtain a yellow oil, which was separated and purified by column chromatography on silica gel, using a mixture of petroleum ether and ethyl acetate at a volume ratio of 20:1 as an eluent, and collected The eluent was evaporated to remove the solvent to obtain 127 mg of yellow oily product with a yield of 85%, which ...

Embodiment 2

[0026] 2-(p-Toluidine) tert-butyl acetate (0.5 mmol, 110.6 mg), N - Add methylaniline (0.6 mmol, 64.2 mg) and methylene blue (0.025 mmol, 8 mg) into a 25 mL two-necked flask, then add acetonitrile (5 mL) as solvent, stir, and irradiate with blue light from a 3W LED lamp Under air atmosphere, react at a temperature of 50°C for 12h. After the reaction, add water and methylene chloride to the reaction system, extract and separate layers, and divide into an aqueous layer and an organic layer. Add anhydrous sodium sulfate to the organic layer for drying , the dried organic layer was concentrated by distillation under reduced pressure to obtain a yellow oil, and the obtained yellow oil was separated and purified by column chromatography on silica gel, and a mixed solution of petroleum ether and ethyl acetate with a volume ratio of 40:1 was used as an eluent. Collect the eluate and evaporate the solvent to obtain 122 mg of yellow solid product with a yield of 75%, namely the target p...

Embodiment 3

[0029] 2-(p-Cymeniline) ethyl acetate (0.5 mmol, 110.6 mg), N - Methylaniline (0.8 mmol, 85.6 mg), methylene blue (0.05 mmol, 16 mg) was added to a 25 mL two-necked flask, and then 1,2-dichloroethane (5 mL) was added as a solvent, stirred, and at a power of 3W Under the blue light from the LED lamp, react at 50°C for 16 hours in the air atmosphere. After the reaction,

[0030] Add water and dichloromethane to the reaction system, extract and separate layers, divide into water layer and organic layer, add anhydrous sodium sulfate to the organic layer to dry, and the dried organic layer is concentrated by vacuum distillation to obtain a yellow oil, and the obtained yellow The oil was separated and purified by column chromatography on silica gel, using a mixture of petroleum ether and ethyl acetate at a volume ratio of 20:1 as the eluent, collecting the eluent and evaporating the solvent to obtain 102.7mg of a yellow oily product, the yield Be 63%, obtain target product, its str...

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Abstract

The invention discloses a synthesis method of α-aryl substituted glycine ester derivatives. The steps are: dissolving the glycine ester compound represented by formula (I), the arylamine represented by formula (II) and the photocatalyst in In an organic solvent, under visible light irradiation, react at 20-80°C for 6-24 h. After the reaction, the reaction system is separated and purified to obtain the target product, which is synthesized to obtain α-aryl-substituted glycine represented by formula (III) Ester derivatives, the reaction formula is as follows: in formula (I), formula (II) and formula (III), R 1 is H, methyl, ethyl, isopropyl, methoxy, chlorine or phenyl; R 2 for C 1 -C 4 the alkyl group; R 3 , R 4 Independently represent H or C 1 -C 6 the alkyl group; R 5 is methyl, chlorine, bromine or fluorine. A photocatalytic synthesis method of α-aryl-substituted glycine ester derivatives of the present invention has the advantages of easy-to-obtain raw materials, good reaction regioselectivity, easy operation, economical and environmental protection, etc., and is a kind of method with good application prospects. Green chemical synthesis method.

Description

technical field [0001] The invention relates to a method for synthesizing alpha-aryl substituted glycine ester derivatives. Background technique [0002] Glycine derivatives are widely used in the fields of medicine and biology, and have very important physiological functions in humans and animals. They can not only participate in the synthesis of proteins and active molecules related to metabolism, but also have liver detoxification and treatment of gastrointestinal tract. function disorder, prevent gastric ulcer and prevent arthritis and other multiple effects. However, the content of glycine derivatives in nature is extremely limited, which seriously affects their application in pharmacological research. Therefore, the synthesis of glycine derivatives by chemical methods has important research significance. [0003] The existing synthetic methods of α-aryl substituted glycine derivatives mainly include the following: preparation by dehydrogenation coupling reaction betwe...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C229/42C07C227/16C07C227/40
CPCC07C227/16C07C227/40C07C2601/14C07C229/42
Inventor 孙彬金灿邓家诚
Owner ZHEJIANG UNIV OF TECH
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