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Preparation method for betulinic acid

A technology of betulinic acid and betulin, which is applied in the field of preparation of semi-synthesized betulinic acid from betulin, can solve the problems of difficult recovery of high-boiling point solvents and solvents, and achieve the effects of easy product purification, short process route and strong reaction specificity

Active Publication Date: 2015-04-15
NORTHEAST FORESTRY UNIVERSITY
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  • Abstract
  • Description
  • Claims
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Problems solved by technology

This method is a heterogeneous reaction, and it is difficult to use a high boiling point solvent for solvent recovery, and this method is only a production method for preparing betulinic acid crude product

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  • Preparation method for betulinic acid

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preparation example Construction

[0024] A preparation method of betulinic acid, using betulin as raw material, comprises the steps carried out in the following order:

[0025] (1) Preparation of crude betulinic acid by oxidation of betulin: dissolving betulin in a water-soluble organic solvent, adding 2,2,6,6-tetramethyl-1-piperidone, sodium bromide, and sodium acetate in sequence Aqueous solution, N-chlorophthalimide, stirred at 0-35°C for 0.5-2 hours, filtered after the reaction, acidified the filtrate with hydrochloric acid until the precipitate precipitated, filtered and washed the obtained precipitate, and dried naturally to obtain birch crude acid;

[0026] (2) Purify the crude betulinic acid to obtain the betulinic acid product: dissolve the crude betulinic acid obtained in step (1) in an organic solvent, add an aqueous solution of inorganic alkali and stir at 50-70°C for 0.5-2 hours, then filter and separate the liquids , the inorganic phase was acidified with hydrochloric acid until precipitation wa...

Embodiment 1

[0033] Dissolve 44.3 grams (0.1moL) betulin in 4430 milliliters of acetone, add 0.156 grams (0.001moL) 2,2,6,6-tetramethyl-1-piperidone, 0.515 grams (0.005moL ) sodium bromide, 4.5 milliliters of sodium acetate aqueous solution with a mass concentration of 15%, 45.5 grams (0.25 moL) of N-chlorophthalimide, stirred and reacted at 25 ° C for 2 hours, filtered, and added to the filtrate Add dilute hydrochloric acid to acidify to pH 3.5, filter, wash the precipitate with distilled water, and air-dry to obtain 41 g of crude betulinic acid. Dissolve the obtained crude betulinic acid in 2050 ml of cyclopentanone, add 41 ml of 30% aqueous sodium hydroxide solution, stir and react at 50°C for 2 hours, filter, add dilute hydrochloric acid to the filtrate to acidify to pH 2.5, and filter , the precipitate was washed with distilled water, air-dried, and recrystallized from methanol to obtain 22.4 grams of betulinic acid product with a purity of 95.9% and a yield of 47%.

Embodiment 2

[0035] Dissolve 44.3 grams (0.1moL) of betulin in 8860 milliliters of tetrahydrofuran, add 0.78 grams (0.005moL) of 2,2,6,6-tetramethyl-1-piperidone, 1.03 grams (0.01moL ) sodium bromide, 10% sodium acetate aqueous solution with a mass concentration of 10 milliliters, 36.4 grams (0.2 moL) of N-chlorophthalimide, stirred and reacted at 35°C for 1 hour and then filtered, and dripped in the filtrate Add dilute hydrochloric acid to acidify to pH 2.5, filter, wash the precipitate with distilled water, and air-dry to obtain 43.9 g of crude betulinic acid. Dissolve the crude betulinic acid obtained in 4390 ml of cyclopentanone, add 200 ml of 30% potassium hydroxide aqueous solution, stir and react at 55°C for 1 hour, filter, add dilute hydrochloric acid to the filtrate to acidify to pH 2.5, and filter , the precipitate was washed with distilled water, air-dried, and recrystallized from methanol to obtain 23.6 grams of betulinic acid product with a purity of 92.9% and a yield of 48%. ...

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Abstract

The invention relates to a preparation method for a betulinic acid. According to the present invention, betulin is adopted as a raw material; the method comprises a process route, wherein the process route comprises the following steps: (1) preparation of a betulinic acid crude product by selective oxidation of the betulin; (2) purification of the betulinic acid crude product to obtain the betulinic acid product. With the present invention, the direct production method for the betulinic acid by selective oxidation of the betulin is provided, the process route is simple, and the produced product is easy to purify.

Description

technical field [0001] The invention relates to a semi-synthetic preparation method of natural compounds, in particular to a preparation method of semi-synthetic betulinic acid from betulin. Background technique [0002] Betulinic acid (betulinic acid, I), also known as betulinic acid, β-betulinic acid, is a secondary metabolite of pentacyclic triterpenoids. It is a needle-like crystal. Molecular formula: C 30 h 48 o 3 , molecular weight 456.71, molecular structure formula: [0003] [0004] Betulinic acid has anti-malarial, anti-inflammatory, anti-HIV activity, and shows cytotoxic activity to a series of tumor cell lines. It is an anti-cancer and anti-AIDS compound with broad application and development prospects. The content of betulinic acid in plants is limited, but the structural analogue of betulinic acid, betulin (betulin, II), has a high content in birch bark, which can reach 10-35%. Betulinic acid can be semi-synthesized through betulin be made of. [0005] ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J63/00
Inventor 阎秀峰杨玉焕王洋丁为民于涛
Owner NORTHEAST FORESTRY UNIVERSITY
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