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Preparation method for abietic acid derivative

A technology of abietic acid and derivatives, which is applied in the field of preparation of abietic acid derivatives, can solve problems such as low yield, low product yield, and easy formation of polymers, and meet the requirements of high yield, improved product purity, and reaction conditions low effect

Active Publication Date: 2015-10-28
XIHUA UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The yield of the whole process route is very low, especially in the reduction reaction step of Huang Minglong, because the reaction temperature is too high, >200°C, it is easy to form polymers, the product yield is very low and the repeatability is not good

Method used

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  • Preparation method for abietic acid derivative
  • Preparation method for abietic acid derivative
  • Preparation method for abietic acid derivative

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] The preparation method of abietic acid derivative comprises the following steps:

[0030] (1) Dissolve abietic acid 1 in a solvent, add alkali under stirring at room temperature, stir for 15 minutes, then add iodoethane, heat up to 60°C for 24 hours, extract, wash, dry, and concentrate to obtain intermediate 2;

[0031] (2) Dissolve intermediate 2 in a solvent, add lithium aluminum tetrahydrogen in an ice bath, stir at room temperature for 4 hours, adjust the pH to 6 with dilute hydrochloric acid, filter and spin the filtrate, extract, wash, dry, and concentrate to obtain Intermediate 3;

[0032] (3) Dissolve the intermediate 3 in the solvent, add p-toluenesulfonyl chloride under stirring in an ice bath, the molar ratio of intermediate 3: p-toluenesulfonyl chloride is 1:3, stir at room temperature for 6 hours, filter, extract, wash , dried and concentrated to obtain intermediate 4;

[0033] (4) Dissolving intermediate 4 in a solvent, adding it to NaI and Zn with stirr...

Embodiment 2

[0038] The preparation method of abietic acid derivative comprises the following steps:

[0039] (1) Dissolve abietic acid 1 in a solvent, add alkali under stirring at room temperature, stir for 15 minutes, then add bromoethane, heat up to 60°C and react for 26 hours, extract, wash, dry, and concentrate to obtain intermediate 2;

[0040] (2) Dissolve intermediate 2 in a solvent, add lithium aluminum tetrahydrogen in an ice bath, stir at room temperature for 3 hours, adjust the pH to 6 with dilute hydrochloric acid, filter and spin the filtrate, extract, wash, dry, and concentrate to obtain Intermediate 3;

[0041] (3) Dissolve the intermediate 3 in the solvent, add p-toluenesulfonyl chloride under ice-bath stirring, the molar ratio of intermediate 3:p-toluenesulfonyl chloride is 1:5, stir at room temperature for 6h, filter, extract, wash , dried and concentrated to obtain intermediate 4;

[0042] (4) Dissolving intermediate 4 in a solvent, adding it to NaI and Zn with stirri...

Embodiment 3

[0047] The preparation method of abietic acid derivative comprises the following steps:

[0048] (1) Dissolve abietic acid 1 in a solvent, add alkali under stirring at room temperature, stir for 15 minutes, then add ethyl chloride, heat up to 60°C and react for 28 hours, extract, wash, dry, and concentrate to obtain intermediate 2;

[0049] (2) Intermediate 2 is dissolved in a solvent, and Lithium Aluminum Hydride is added under an ice bath, ， Stir the reaction at room temperature for 4 hours, adjust the pH to 6 with dilute hydrochloric acid, filter and spin the filtrate, extract, wash, dry, and concentrate to obtain intermediate 3;

[0050] (3) Dissolve the intermediate 3 in the solvent, add p-toluenesulfonyl chloride under ice-bath stirring, the molar ratio of intermediate 3: p-toluenesulfonyl chloride is 1:6, stir at room temperature for 6h, filter, extract, wash , dried and concentrated to obtain intermediate 4;

[0051] (4) Dissolving intermediate 4 in a solvent, adding...

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Abstract

The invention belongs to the technical field of chemical pharmacy, and particularly discloses a preparation method for an abietic acid derivative. Abietic acid 1 is dissolved in solvent, alkali is added, halogenated hydrocarbon is added, and then an intermediate 2 is obtained; the intermediate 2 is dissolved in solvent, lithium aluminum hydride is added, the pH is regulated to 6 through diluted hydrochloric acid, and then an intermediate 3 is obtained; the intermediate 3 is dissolved in solvent, paratoluensulfonyl chloride is added, and then an intermediate 4 is obtained; the intermediate 4 is dissolved in solvent, NaI and Zn are added, and then an intermediate 5 is obtained; the intermediate 5 is dissolved in solvent, hydrogen bromide is added, washing is performed through frozen glacial acetic acid, and then an intermediate 6 is obtained; the intermediate 6 is dissolved in solvent, alkali is added, diluted hydrochloric acid is added to regulate the PH to 2-3, and then an intermediate 7 is obtained; the intermediate 7 is dissolved in solvent, selenium dioxide is added, and a product 8 is obtained. According to the preparation method of the abietic acid derivative, the yield is high; particularly, Huang-Minlon reduction reaction needing high temperature is avoided, so that the requirement for reaction conditions is low; in addition, the product purity is greatly improved.

Description

technical field [0001] The invention belongs to the technical field of chemical pharmacy, in particular to a preparation method of abietic acid derivatives. Background technique [0002] Abietic acid is used as a traditional Chinese medicine because it has good biological activity, many of which are agricultural chemicals, and its derivatives are mostly used in the synthesis of medicines. At present, the synthesis process of abietic acid derivatives reported in domestic and foreign literature is to first esterify the carboxyl group of abietic acid, and then construct an aromatic ring through addition, elimination, and oxidation of the conjugated double bond, and finally the carboxyl group is reduced by lithium aluminum hydride, Oxidation, Huang Minglong reduction, and finally get C-4 abietic acid derivatives with gem dimethyl. The yield of the whole process route is very low, especially in the reduction reaction step of Huang Minglong, because the reaction temperature is to...

Claims

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Application Information

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IPC IPC(8): C07C29/48C07C33/34
CPCC07C1/30C07C1/322C07C17/08C07C29/147C07C29/48C07C67/11C07C303/28C07C2603/26C07C33/34C07C13/60C07C23/44C07C309/73C07C33/14C07C69/753
Inventor 钱珊何彦颖陈泉龙张曼王伟袁陈
Owner XIHUA UNIV