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Cannabidiol intermediate and preparation method and application thereof

A cannabidiol and intermediate technology, which is applied to the cannabidiol intermediate and its preparation method and application field, can solve the problems of large limitations in industrialized production, cumbersome steps, etc., and achieves good industrial application prospects, process improvement, and price. low cost effect

Inactive Publication Date: 2019-05-10
JIANGSU JIMING PHARMA TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0012] In addition to the above two chemical synthesis methods, there are some reports in the literature that cannabidiol is obtained by biological extraction, but the steps of such methods are relatively cumbersome, and the limitations of industrial production are too large

Method used

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  • Cannabidiol intermediate and preparation method and application thereof
  • Cannabidiol intermediate and preparation method and application thereof
  • Cannabidiol intermediate and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0044] compound 3 Preparation of:

[0045] Add 31.6g of tert-butyl acetoacetate and 100ml of methanol into a 500mL single-necked flask; add dropwise 47.9mL of 28% sodium methoxide methanol solution (about 10min, no obvious exotherm); N 2 Under protection, 31.2 g of trans-2-octene methyl ester was added dropwise (the solution was completely clear when about half of it was added); after the addition, the reaction was stirred under reflux for 2.5 hours; the solvent was concentrated under reduced pressure at room temperature; 300.0 mL of water was added , dissolved clear;

[0046] Extract with 80.0 mL x3 of dichloromethane; the aqueous phase was adjusted to pH=4 with concentrated hydrochloric acid, and an off-white solid precipitated;

[0047] Filtered compound 3 50.8g, yield 90%, purity 98.5%;

[0048] compound 4 Preparation of:

[0049] Add compound to 500mL reaction vial 3 47.0g and DMF78.0mL, stir to dissolve;

[0050] Add bromine DMF solution (26.0g dissolved in DMF 8...

Embodiment 2

[0055] compound 3 Preparation of:

[0056] Add 31.6g of tert-butyl acetoacetate and 100ml of methanol into a 500mL single-necked flask; add dropwise 47.9mL of 28% sodium methoxide methanol solution (about 10min, no obvious exotherm); N 2 Under protection, 31.2 g of trans-2-octene methyl ester was added dropwise (the solution was completely clear when about half of it was added); after the addition, the reaction was stirred under reflux for 2.5 hours; the solvent was concentrated under reduced pressure at room temperature; 300.0 mL of water was added , dissolved clear;

[0057] Extract with ethyl acetate 80.0mL x3; the aqueous phase was adjusted to pH=4 with 6N sulfuric acid, and an off-white solid was precipitated; the compound was obtained by filtration 3 51.2g, yield 91%, purity 98.2%;

[0058] compound 4 Preparation of:

[0059] Add compound to 500mL reaction vial 3 47.0g and DMF 78.0mL, stir to dissolve;

[0060] Add bromine DMF solution (26.0g dissolved in DMF 86....

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Abstract

The invention discloses a cannabidiol intermediate and a preparation method and application thereof. A high-quality intermediate can be obtained by using trans-2-octenyl methyl ester and tert-butyl acetoacetate as raw materials through two-step reaction of cyclization and aromatization, and the intermediate has a structural formula as shown in specification. The intermediate in each step can be purified through recrystallization, single impurities can reach the index of the intermediate of crude drug, the total yield of qualified pure crude drug prepared from the intermediate prepared by the method can reach 50-60%, the process is obviously improved, and the method has a good industrial application prospect.

Description

technical field [0001] The invention relates to a cannabidiol intermediate and its preparation method and application, belonging to the technical field of organic synthesis. Background technique [0002] The alias of cannabidiol is L-trans-cannabidiol, and its English name is (-)-Cannabidiol. It is a very marketable raw material drug. The structural formula of the compound is: [0003] [0004] Cannabidiol is the main non-psychoactive component in industrial hemp. It has the effect of reducing inflammation, convulsions and anxiety, pain and vomiting in medicine, and has remarkable effects in antidepressant, antiepileptic, anticancer, pain relief and sedation. On June 26, 2018, the U.S. Food and Drug Administration approved Epidiolex (cannabidiol) [CBD] oral solution for the treatment of two rare and severe forms of epilepsy, associated with Lennox-Gastaut syndrome and Dravet syndrome, in patients two years of age and older seizures, which makes the market prospect of thi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C67/31C07C69/84C07C37/00C07C39/23
Inventor 陈剑戈李斌峰顾志锋
Owner JIANGSU JIMING PHARMA TECH
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