Preparation method of cannabidiol compound

A compound and catalyst technology, applied in the field of preparation of cannabidiol compounds, can solve the problem that the yield is only 46.7%, achieve the effect of improving chiral selectivity, avoiding oxidation impurities and polymerization impurities

Active Publication Date: 2020-12-08
CHENGDU HYPERWAY PHARM CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

WO2017194173A1 reported that the first step was Friedel-Crafts alkylation reaction using boron trifluoride ether as a catalyst, and the crude product obtained by hydrolysis and decarboxylation of potassium hydroxide needed to be recrystallized once at high temperature and reduced pressure to obtain a CBD product with a purity of 99%. US2007093665A1 reported that using scandium trifluoromethanesulfonate as a catalyst, the final product can be crystallized to obtain a CBD product with a purity of 99.8%, but the two-step yield is only 46.7%

Method used

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  • Preparation method of cannabidiol compound
  • Preparation method of cannabidiol compound
  • Preparation method of cannabidiol compound

Examples

Experimental program
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Effect test

preparation example 1

[0061] Preparation Example 1 Synthesis of Chiral Catalyst TfOH-IMID-4

[0062] S1: to MeNH 2 L-valine methyl ester hydrochloride (8.4 g, 100 mmol) was added to the ethanol solution (8.0 M, 50 ml), and the reaction was carried out under stirring at room temperature until the reaction of L-valine methyl ester was completed as monitored by TLC. It was concentrated under reduced pressure to remove ethanol and methylamine to obtain 8.5 g of (S)-2-amino-3-methylbutyrylmethylamide as a colorless oil. The oily substance was dissolved in methanol (100 mL), acetone (59 mL, 800 mmol) and triethylamine (11.1 mL, 80 mmol) were added, the temperature was refluxed for 24 h, and the crude product obtained by concentrating under reduced pressure was purified by column to obtain a colorless oil. IMID-4 (8.3g);

[0063] S2: The obtained IMID-4 was dissolved in EA (50 mL), and TfOH (15 g, 100 mmol) was diluted with EA (20 mL) and slowly added dropwise to the reaction, the above suspension was c...

preparation example 2

[0064] Preparation Example 2 Synthesis of Chiral Catalyst TFA-IMID-4

[0065] The preparation method of IMID-4 is the same as that of Preparation Example 1. The obtained IMID-4 was dissolved in EA (50 mL), and TFA (9.4 g, 100 mmol) was diluted with EA (20 mL) and slowly added dropwise to the reaction, and the above was filtered. The suspension was washed with EA and the filter cake was dried to obtain 12.1 g of white solid TFA-IMID-4 product.

preparation example 3

[0066] Preparation Example 3 Synthesis of Chiral Catalyst TsOH-IMID-4

[0067] The preparation method of IMID-4 was the same as that of Preparation Example 1. The obtained IMID-4 was dissolved in EA (50 mL), and TsOH (18 g, 100 mmol) was diluted with EA (20 mL) and slowly added dropwise to the reaction. The suspension was washed with EA and the filter cake was dried to obtain 15.2 g of white solid TsOH-IMID-4 product.

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Abstract

The invention discloses a preparation method of a compound with a general formula I or pharmaceutically acceptable salts, stereoisomers, esters, prodrugs and solvates thereof, which comprises the following steps: (1) by using a compound A and (1S, 4R) 1methyl 4 (1methyl vinyl) 2cyclohexene 1alcohol as raw materials, carrying out coupling under the action of a chiral imidazolone salt catalyst to obtain a compound B; carrying out sodium sulfite dehalogenation and alkali washing to obtain an intermediate 1; (2) heating the intermediate 1 to 80100 DEG C under the action of DMSO, lithium chloride and an antioxidant, reacting, and recrystallizing to obtain a compound with a general formula I;.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of a cannabidiol compound. Background technique [0002] Cannabidiol (CBD) and tetrahydrocannabinol (THC) are the main chemical components contained in cannabis. THC is neuroactive and can be used to treat vomiting caused by cancer. THC is hallucinogenic and addictive. Different from THC, CBD is a non-addictive ingredient in marijuana. It has the ability to block the adverse effects of certain polyphenols on the human nervous system. It can block breast cancer metastasis, treat epilepsy, resist rheumatoid arthritis, and resist insomnia. A series of physiologically active functions. The drug Epidiolex (the main ingredient is CBD) developed by British GW Pharmaceuticals has been sold in the European and American markets, mainly for the treatment of infantile severe myoclonic epilepsy (Dravet) and childhood diffuse chronic spike-slow wave ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C37/50C07C39/23C07C67/343C07C69/94B01J31/02
CPCC07C37/50C07C67/343B01J31/0235C07C2601/16C07B2200/07B01J2231/42C07C39/23C07C69/94Y02P20/52
Inventor 卓国清夏鸿林波程海婷冯世成李英富
Owner CHENGDU HYPERWAY PHARM CO LTD
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