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Synthesis method of D,L-danshensu isopropyl ester

A technology of danshensu isopropyl ester and scrambled danshensu, which is applied in the field of drug synthesis, can solve the problems such as the yield to be improved, and achieve the effects of being easy to handle or recover, having little environmental pollution and reducing production costs.

Active Publication Date: 2014-08-13
NORTHWEST UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

In view of the industrial cost problem of this method, the yield still needs to be improved

Method used

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  • Synthesis method of D,L-danshensu isopropyl ester
  • Synthesis method of D,L-danshensu isopropyl ester
  • Synthesis method of D,L-danshensu isopropyl ester

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] (1) Synthesis of 3,4-dibenzyloxybenzaldehyde:

[0057] Dissolve 55.2g (0.40mol) of protocatechualdehyde with 600ml N,N-dimethylformamide, slowly add 116.0g (0.92mol) of benzyl chloride to it, and then add anhydrous K 2 CO 3 165.6g (1.2mol), stirring reaction at room temperature for 2 hours, then adding K 2 CO 3 55.2g (0.40mol), heated at 120°C for 2 hours, cooled to room temperature, filtered with suction, the filtrate was added to ice water, acidified with dilute hydrochloric acid, a yellow precipitate was produced, filtered with suction, washed with ice water to obtain compound 3,4-dibenzyl Oxybenzaldehyde 122.1g, the yield is 96%.

[0058] (2) Synthesis of isopropyl chloroacetate:

[0059] Add 56.4 g (0.5 mol) of chloroacetyl chloride to the mixed solution [the mixed solution is 400 mL of dichloromethane, 30.0 g (0.5 mol) of isopropanol and 50.5 g (0.5 mol) of triethylamine] at 0° C. Stir the reaction for 2 h, add 200 mL of water to the reaction solution, wash w...

Embodiment 2

[0073] This embodiment differs from Embodiment 1 in that:

[0074] (1) Synthesis of 3-(3,4-dibenzyloxyphenyl) isopropyl glycidate:

[0075] Dissolve 12.2 g (0.225 mol) of sodium methoxide in 150 mL of methanol to obtain solution 1;

[0076] Dissolve 47.7g (0.15mol) of 3,4-dibenzyloxybenzaldehyde and 20.5g (0.15mol) of isopropyl chloroacetate in 150mL of dioxane to obtain solution 2;

[0077] Drop solution 2 into solution 1 within 30 mm, stir overnight at room temperature, add the reaction solution to 100 mL of ice water, adjust to neutral with hydrochloric acid, extract with dichloromethane (200 mL×4), combine the organic phases, wash with anhydrous sodium sulfate After drying and concentration under reduced pressure, the crude product was recrystallized from isopropanol / petroleum ether to obtain 38.3 g of off-white solid with a yield of 61%.

[0078] (2) Synthesis of Danshensu Isopropyl Ester:

[0079] Dissolve 18g of 3-(3,4-dibenzyloxyphenyl)glycidic acid isopropyl ester ...

Embodiment 3

[0081] This embodiment differs from Embodiment 1 in that:

[0082] (1) Synthesis of 3-(3,4-dibenzyloxyphenyl) isopropyl glycidate:

[0083] Dissolve 21.6 g (0.225 mol) of sodium tert-butoxide in 150 mL of tert-butanol to obtain solution 1;

[0084] Dissolve 47.7g (0.15mol) of 3,4-dibenzyloxybenzaldehyde and 20.5g (0.15mol) of isopropyl chloroacetate in 150mL of dioxane to obtain solution 2;

[0085] Drop solution 2 into solution 1 within 30 mm, stir overnight at room temperature, add the reaction solution to 100 mL of ice water, adjust to neutral with hydrochloric acid, extract with dichloromethane (200 mL×4), combine the organic phases, wash with anhydrous sodium sulfate After drying and concentration under reduced pressure, the crude product was recrystallized from isopropanol / petroleum ether to obtain 41.4 g of off-white solid with a yield of 66%.

[0086] (2) Synthesis of Danshensu Isopropyl Ester:

[0087] Dissolve 6g of 3-(3,4-dibenzyloxyphenyl)glycidyl isopropyl in 7...

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Abstract

The invention relates to a synthesis method of D,L-danshensu isopropyl ester. The method comprises taking protocatechuic aldehyde as an initial raw material, protecting phenolic hydroxyl by benzyl, carrying out Darzens epoxidation, followed by carrying out catalytic reduction with palladium catalyst / hydrogen or Raney nickel / hydrogen, and thus obtaining the D,L-danshensu isopropyl ester. The purity of the product synthesized by the method can reach 98%, and the yield can reach 55%. Moreover, the synthesis method has the advantages of simple and easily obtained raw materials, short routes and high yield, and is suitable for large-scale industrialized production.

Description

technical field [0001] The invention relates to a synthesis method of danshensu isopropyl ester, which can be used for treating or preventing cardiovascular and cerebrovascular diseases; it belongs to the technical field of medicine synthesis. Background technique [0002] Helicodanshensu isopropyl ester, the chemical name is (±)-3',4'-dihydroxyphenyl-2-hydroxypropionate isopropyl ester, which is a "jun-shi" drug pair (Danshen-borneol, Danshen- Sandalwood and Danshen-Alfalfa) effector substances metabolized in the body. Its pharmacological studies have shown that Danshensu isopropyl ester has protective effects on the heart function of hypoxic rats, dilating blood vessels, anti-myocardial fibrosis, anti-cerebral ischemia, anti-oxidation, and anti-heart rhythm caused by exogenous free radicals. Disorders and the treatment of ischemic myocardial infarction caused by diabetes. [0003] Chinese patent application (publication number: CN1583710A) discloses a reaction of protoca...

Claims

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Application Information

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IPC IPC(8): C07C69/732C07C67/327C07C67/31C07C69/63C07C67/14
CPCC07C45/64C07C67/14C07C67/31C07C67/327C07D301/02C07D303/48C07C69/732C07C69/63C07C47/575
Inventor 郑晓晖白亚军张群正南叶飞刘佩秦方刚高蓉
Owner NORTHWEST UNIV
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