Preparation method and intermediate of stearyl glycyrrhetinate

A technology of octadecyl glycyrrhetinate and glycyrrhetinic acid, applied in the directions of steroids, organic chemistry, etc., can solve the problems of high market price, the output can not meet the market demand, etc., and achieves low production cost, easy promotion, and stability. Good results

Active Publication Date: 2016-09-28
亿利耐雀生物科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

At present, due to the limitations of the preparation method and production conditions, there is no mature process for mass production of stearyl glycyrrhetinate, so its output is far from meeting the market demand, and the market price is too high
[0005] The invention provides a new method for chemically preparing octadecyl glycyrrhetinate. The preparation method has high yield, novel process, simple operation, energy saving and environmental protection, and has good practicability. At present, there is no relevant patent report Preparation method for obtaining octadecyl glycyrrhetinate with high yield by chemical synthesis

Method used

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  • Preparation method and intermediate of stearyl glycyrrhetinate
  • Preparation method and intermediate of stearyl glycyrrhetinate
  • Preparation method and intermediate of stearyl glycyrrhetinate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0030] Add 100 ml of ethyl acetate and 50 ml of triethylamine to 1 mol of glycyrrhetinic acid and 1 mol of p-toluenesulfonyl chloride, stir at room temperature (25°C) for 2 hours, a white solid precipitates, and filter. Add 1 mol of the above white solid, 1 mol of stearyl alcohol, and 1.5 mol of potassium carbonate to 200 ml of DMF and react at 70°C for 5 hours, add water, extract with ethyl acetate, and dry the organic phase to obtain 685.9 g of the product with a yield of 95%.

[0031] Detection method: Shimadzu LC-20AT liquid chromatograph, with InertSustain C18 column (4.6×150mm×5μm) as chromatographic column, acetonitrile:1mol / L phosphoric acid aqueous solution (85:15) as mobile phase, detection wavelength 254nm, The flow rate is 1.0ml / min. HPLC purity 98.3%.

Embodiment 2

[0033] Add 150 ml of ethyl acetate and 50 ml of triethylamine to 1 mol of glycyrrhetinic acid and 1 mol of p-toluenesulfonyl chloride, stir at room temperature for 2 hours, a white solid precipitates, and filter. 1 mol of white solid, 1 mol of stearyl alcohol, and 2 mol of potassium carbonate were added to 200 ml of DMF to react at 70° C. for 5 hours, water was added, extracted with ethyl acetate, and the organic phase was dried to obtain 649.8 g of the product with a yield of 90%.

[0034] Detection method: Shimadzu LC-20AT liquid chromatograph, with InertSustain C18 column (4.6×150mm×5μm) as chromatographic column, acetonitrile:1mol / L phosphoric acid aqueous solution (85:15) as mobile phase, detection wavelength 254nm, The flow rate is 1.0ml / min, and the HPLC purity is 92.9%.

Embodiment 3

[0036] Add 100 ml of ethyl acetate and 50 ml of triethylamine to 1 mol of glycyrrhetinic acid and 1.5 mol of p-toluenesulfonyl chloride, stir at room temperature for 2 hours, a white solid precipitates, and filter. 1 mol of the above white solid, 1 mol of stearyl alcohol, and 1.5 mol of potassium carbonate were added to 250 ml of DMF to react at 70° C. for 5 hours, add water, extract with ethyl acetate, and dry to obtain 664.24 g of the product with a yield of 92%.

[0037] Detection method: Shimadzu LC-20AT liquid chromatograph, with InertSustain C18 column (4.6×150mm×5μm) as chromatographic column, acetonitrile:1mol / L phosphoric acid aqueous solution (85:15) as mobile phase, detection wavelength 254nm, The flow rate is 1.0ml / min, and the HPLC purity is 93.5%.

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Abstract

The invention discloses a preparation method and an intermediate of stearyl glycyrrhetinate. The preparation method comprises the following steps: (1) in an organic solvent, carrying out reaction on glycyrrhetinic acid and p-methyl benzene sulfonyl chloride in the presence of organic alkali, and after the reaction finishes, filtering to obtain a white solid; (2) in an organic solvent, carrying out reaction on the white solid and stearyl alcohol in the presence of alkali, and after the reaction finishes, separating the stearyl glycyrrhetinate from the system. The invention also discloses an intermediate of the stearyl glycyrrhetinate. The method disclosed by the invention has the advantages of high yield, fewer impurities and low cost.

Description

technical field [0001] The invention relates to a preparation method of stearyl glycyrrhetinate, in particular to a method for preparing stearyl glycyrrhetinate with high yield, less impurities and low cost and an intermediate thereof. Background technique [0002] Licorice is the root and rhizome of Glycyrrhiza uralensis Fisch, Glycyrrhiza inflata Bat, or Glycyrrhiza glabra L, which are mainly produced in Inner Mongolia, Xinjiang, Gansu and other places. Licorice has a long history of being used as medicine, and "Shen Nong's Materia Medica" listed it as the best medicine, and ancient medical scientists honored it as "the old man of the country". Because of its precious resources, it is listed as the second-class national protected wild medicinal material by the country. [0003] Glycyrrhizic acid is the main active ingredient of licorice. The aglycone of glycyrrhizic acid is glycyrrhetinic acid. In the human body, glycyrrhizic acid is hydrolyzed by gastric acid or decompos...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J63/00
CPCC07J63/008
Inventor 王陈茹袁继文金显友钟慧杨永安
Owner 亿利耐雀生物科技有限公司
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