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Method for synthesizing mephenesin carbamate by using carbon dioxide, amine and aryl diazoacetate

A kind of technology of diazoacetate, carbamate

Active Publication Date: 2018-02-09
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] Although some progress has been made in the synthesis of carbamates using carbon dioxide, there are still shortcomings such as narrow substrate applicability, poor functional group tolerance, or low selectivity.

Method used

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  • Method for synthesizing mephenesin carbamate by using carbon dioxide, amine and aryl diazoacetate
  • Method for synthesizing mephenesin carbamate by using carbon dioxide, amine and aryl diazoacetate
  • Method for synthesizing mephenesin carbamate by using carbon dioxide, amine and aryl diazoacetate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] The synthesis of azepane-1-carboxylic acid (2-ethoxy-2-oxo-1-phenyl) ethyl ester comprises the steps:

[0048] In the autoclave, add 0.2mmol ethyl 2-diazo-2-phenylacetate, 0.02mmol silver carbonate, 3mL acetonitrile and 0.6mmol cycloheximide, and then slowly fill in carbon dioxide to make the pressure reach 4MPa, at 80 ℃ and stirred for 12 hours; after the reaction, stop heating and stirring, cool to room temperature, slowly release unreacted carbon dioxide to normal pressure, dilute the reaction solution with ethyl acetate, filter, then distill off the solvent under reduced pressure to obtain a crude product, and then Separation and purification by column chromatography, the eluent of column chromatography is sherwood oil with a volume ratio of 20:1: ethyl acetate mixed solvent to obtain the target product azepane-1-carboxylic acid (2-ethoxy -2-oxo-1-phenyl)ethyl ester, yield 45%.

[0049] The hydrogen spectrogram and the carbon spectrogram of described obtaining prod...

Embodiment 2

[0054] The synthesis of azepane-1-carboxylic acid (2-ethoxy-2-oxo-1-phenyl) ethyl ester comprises the steps:

[0055] In the autoclave, add 0.2mmol ethyl 2-diazo-2-phenylacetate, 0.02mmol silver fluoride, 3mL acetonitrile and 0.6mmol cycloheximide, and then slowly fill in carbon dioxide to make the pressure reach 4MPa. Stir and react at 80°C for 12 hours; after the reaction, stop heating and stirring, cool to room temperature, slowly release unreacted carbon dioxide to normal pressure, dilute the reaction solution with ethyl acetate, filter, and then distill off the solvent under reduced pressure to obtain a crude product. Separation and purification by column chromatography, the eluent of column chromatography is sherwood oil with a volume ratio of 20:1: ethyl acetate mixed solvent to obtain the target product azepane-1-carboxylic acid (2-ethoxy yl-2-oxo-1-phenyl)ethyl ester, yield 78%.

[0056] The hydrogen spectrogram and the carbon spectrogram of the resulting product are...

Embodiment 3

[0059] The synthesis of azepane-1-carboxylic acid (2-ethoxy-2-oxo-1-phenyl) ethyl ester comprises the steps:

[0060] In the autoclave, add 0.2mmol ethyl 2-diazo-2-phenylacetate, 0.01mmol silver acetate, 3mL acetonitrile and 0.2mmol cycloheximide, then slowly fill in carbon dioxide to make the pressure reach 6MPa, at 80 ℃ and stirred for 12 hours; after the reaction, stop heating and stirring, cool to room temperature, slowly release unreacted carbon dioxide to normal pressure, dilute the reaction solution with ethyl acetate, filter, then distill off the solvent under reduced pressure to obtain a crude product, and then Separation and purification by column chromatography, the eluent of column chromatography is sherwood oil with a volume ratio of 20:1: ethyl acetate mixed solvent to obtain the target product azepane-1-carboxylic acid (2-ethoxy -2-oxo-1-phenyl)ethyl ester, yield 18%.

[0061] The hydrogen spectrogram and the carbon spectrogram of the resulting product are show...

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Abstract

The invention discloses a method for synthesizing mephenesin carbamate by using carbon dioxide, amine and aryl diazoacetate. The method comprises the following steps: in a high-pressure reactor, dissolving the aryl diazoacetate and the amine into a solvent, then adding a silver catalyst, introducing the carbon dioxide, heating and reacting under the stirring condition; after the reaction is ended,stopping heating and stirring, cooling, and slowly releasing unreacted carbon dioxide; diluting the reaction solution with ethyl acetate, filtering and removing the solvent by reduced pressure distillation to obtain a crude product; then carrying out column chromatography purification to obtain the mephenesin carbamate. The synthetic method disclosed by the invention has the advantages of simpleoperation, low-price and easily-obtained raw materials such as the carbon dioxide and the amine, high economy of reaction atoms, good adaptability of functional groups, wide applicability of a substrate, relative environment friendliness, facilitation for industrial production and good application prospect in organic synthesis.

Description

technical field [0001] The invention relates to the technical field of carbamate synthesis, in particular to a method for synthesizing carbamate by utilizing carbon dioxide, amine and aryl diazoacetate. Background technique [0002] Carbamates are an important class of compounds that exist in many natural products, such as physostigmine. Due to its broad-spectrum biological and pharmaceutical activities, it is widely used in pesticides and medicine. There are more than 50 varieties of carbamate pesticides, including the insecticides carbofuran, aldicarb, yechansan, pirimicarb, and the herbicide mezamid (Z.Li, Z.Wu and F.Luo , J.Agric.Food Chem.2005, 53, 3872; L.Chen, Z.Huang, Q.Wang, J.Shang, R.Huang and F.Bi, J.Agric.Food Chem.2007, 55, 2659) . Carbamate medicines include the well-known anti-HIV drug darunavir (Prezista) and the drug solifenacin succinate (VESIcare) for the treatment of frequent urination and urinary incontinence (A.Joshi, J.-B.Véron, J. .Unge, Rosenq...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D295/205C07C271/12C07C269/04C07B43/00
CPCC07B43/00C07C269/04C07D295/205C07C271/12
Inventor 戚朝荣颜东豪熊文芳
Owner SOUTH CHINA UNIV OF TECH
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