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Resorcinol derivative and preparation method thereof

A compound and general formula technology, applied in the field of resorcinol derivatives and its preparation, can solve problems such as low product yield, low reaction regioselectivity, and difficult routes

Active Publication Date: 2020-12-11
TOPHARMAN SHANGHAI +2
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] The existing methods all have certain shortcomings, such as low reaction regioselectivity, low product yield, cumbersome product separation and purification process, and difficult derivation and expansion of the route.

Method used

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  • Resorcinol derivative and preparation method thereof
  • Resorcinol derivative and preparation method thereof
  • Resorcinol derivative and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0097] Embodiment 1: the preparation of compound I-1

[0098]

[0099] Phloroglucinol (50.4 g, 400 mmol) was added to a reaction flask with a constant pressure funnel. The air was removed under vacuum and replaced with nitrogen three times, the solvent tetrahydrofuran (150 mL) was added and stirred well until the solid dissolved and became clear. Then boron trifluoride-diethyl ether (2.85 g, 20 mmol) was added to the solution, and after stirring evenly, the reaction temperature was lowered to -5~5°C. Then a solution of trans-menthyl-2,8-dien-1-ol (4.04g, 40mmol) in tetrahydrofuran (50mL) was slowly added dropwise from a constant pressure funnel to the mixture under stirring at -5~5°C, Keep the reaction temperature at -5°C to 5°C for 4 hours. Saturated aqueous sodium bicarbonate (20 mL) was added to quench the reaction, and the reaction mixture was warmed to 20°C-25°C and stirred for half an hour. The aqueous phase was separated and discarded, the organic phase was distil...

Embodiment 2

[0101] Embodiment 2: the preparation of compound II-1

[0102]

[0103] Add compound I-1 (37.2g, 143mmol) and dichloromethane (80mL) into a reaction flask with a constant pressure funnel, add 2,6-lutidine (16.7g, 156mmol) and stir at room temperature . Add trifluoromethanesulfonic anhydride (36.6 g, 130 mmol) and dichloromethane (80 mL) into a constant pressure funnel and mix well. Slowly add the trifluoromethanesulfonic anhydride solution to the reaction under stirring at -20~-15°C, and the dropwise addition is completed in about 1 hour, then the reaction temperature is raised to 0~5°C and the reaction is continued for 3~4 hours. The reaction mixture was warmed up to room temperature 20-25°C, and dilute hydrochloric acid (1M, 35 mL) was added with stirring to quench the reaction and adjust the pH value to 1-2. After fully stirring, let it stand for liquid separation, separate the liquid and discard the aqueous phase. The organic phase was washed once with water, then to...

Embodiment 3

[0105] Embodiment 3: the preparation of compound III-1

[0106]

[0107] Add compound II-1 (3.92g, 10mmol) and dichloromethane (10mL) into a reaction flask with a constant pressure funnel at room temperature and stir until it dissolves and becomes clear, then add N,N-dimethylaminopyridine (122mg, 1mmol) and triethylamine (3.03g, 30mmol) and stirred evenly. Add pivaloyl chloride (3.01 g, 25 mmol) and dichloromethane (80 mL) into a constant pressure funnel and mix well. The pivaloyl chloride solution was slowly added dropwise to the reaction with stirring at room temperature, and the dropwise addition was completed in about 1 hour, and then the reaction was continued at room temperature for 10 to 12 hours. Dilute hydrochloric acid (1M, 15mL) was added under stirring to quench the reaction and adjust the pH to 1-2. After fully stirring, let it stand for liquid separation, separate the liquid and discard the aqueous phase. Saturated aqueous sodium bicarbonate (20 mL) was add...

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Abstract

The invention relates to a resorcinol derivative and a preparation method thereof. According to the invention, the synthesis method can be very simply and conveniently expanded and applied to synthesis and preparation of other derivatives and analogues of cannabidiol, so that the selectivity is greatly improved, the generation of regioisomers and disubstituted byproducts is avoided to the greatestextent, and the yield is remarkably improved; the method has the advantages of low material cost, few pollutants, simplicity and convenience in operation, easiness in expanded application of a synthetic route and the like; and the method specifically designed by the invention can reduce byproducts, so that the method can be carried out by using a one-pot method so as to greatly reduce the productand energy consumption during purification by using a step-by-step method and greatly reduce pollutants.

Description

technical field [0001] The invention belongs to the field of chemical synthesis, and in particular relates to a resorcinol derivative and a preparation method thereof. Background technique [0002] Resorcinol compounds or their derivatives are a large family of compounds, such as resorcinol, including many natural product molecules, physiologically active molecules, active pharmaceutical ingredients and their prodrug compounds. One of the important members is the drug cannabidiol (CBD). Cannabidiol (CBD) is a non-addictive component in marijuana, which has no hallucinogenic effect and is widely used in the medical field. The application includes protective effects on the nervous system, such as anti-spasmodic, anti-anxiety, anti-epileptic, analgesic, anti-inflammatory, anti-rheumatic and other positive pharmacological effects. Therefore, it can be used in the treatment of various difficult diseases. In addition, a series of resorcinol compounds or their derivatives have a...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/65C07C309/73C07C303/30C07C303/28C07C69/28C07C67/293C07C37/11C07C39/23
CPCC07C309/65C07C309/73C07C67/293C07C37/11C07C69/28C07C39/23Y02P20/55
Inventor 孙长亮朱富强公绪栋蒋翔锐田广辉沈敬山
Owner TOPHARMAN SHANGHAI
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