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Synthetic method for leonurine

A technology of motherwort and synthesis method, which is applied in chemical instruments and methods, preparation of organic compounds, preparation of aminohydroxy compounds, etc., can solve the problems that starting materials are not easy to obtain, difficult to produce on a large scale, and high requirements for reaction conditions, Achieving excellent synthetic route, suitable for large-scale production, and more controllable effects

Active Publication Date: 2017-06-20
绵阳市润土农业科技开发有限公司
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0008] The starting materials of the above three preparation methods are not easy to obtain, and the reaction conditions require high
[0009] In addition, it has been reported that the cheap 4-aminobutyric acid can be produced through amino-protected reduction, but it can only be produced in a small amount, and it is difficult to achieve large-scale production

Method used

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  • Synthetic method for leonurine
  • Synthetic method for leonurine
  • Synthetic method for leonurine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0056] Embodiment 1: the synthesis of gamma-hydroxybutyric acid amide

[0057] Disperse 250 g (3.0 mol) of γ-butyrolactone in 1000 mL of ammonia water (28%), stir overnight, monitor the reaction by TLC, filter to obtain a pure white solid, figure 2 and image 3 Be respectively the carbon nuclear magnetic resonance spectrum and the hydrogen nuclear magnetic resonance spectrum of the pure white solid obtained, by figure 2 and image 3 The pure white solid product was identified as gamma-hydroxybutyric acid amide. The theoretical yield should be 250g, but the actual yield is 230g, the yield is 92%.

Embodiment 2

[0058] Embodiment 2: the synthesis of acetyl syringic acid (I)

[0059] Disperse 198g (1.0mol) of syringic acid in 1000mL of dichloromethane, add 97.6g (0.8mol) of 4-dimethylaminopyridine and stir evenly, slowly add 122.5g (1.2mol) of acetic anhydride dropwise at room temperature and stir for 20 hours, After spin-drying dichloromethane, after adding 900ml dehydrated ethanol thermally dissolving, add 600ml water again and stir evenly static crystallization, suction filtration, filter cake is washed once with 200ml water, oven dry obtains the compound (I) of 208g light brown crystal altogether, The theoretical yield should be 240g, and the yield is 86.6%.

Embodiment 3

[0060] Embodiment 3: the synthesis of acetylated syringyl ester (II)

[0061] Take 0.2mol (48g) of acetylsyringic acid (I), add 500ml of dichloromethane, successively add 0.25mol (47.75g) EDCI, 0.25mol (34g) HOBT and 0.25mol (34g) DIPEA, stir at room temperature for 1 hour, slowly add γ -Hydroxybutyric acid amide 0.25mol (26g), stirred at room temperature for 6h, added 200ml of water to quench the reaction, extracted, washed with saturated brine, and concentrated under reduced pressure to obtain 57g of compound (II) as a pale yellow solid.

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Abstract

The invention relates to the technical field of organic chemistry, in particular to a synthetic method for leonurine. Gamma-butyrolactone is used as a starting material to be subjected to ammonolysis to obtain gamma-hydroxybutyric acid amide; the gamma-hydroxybutyric acid amide and acetyl syringic acid are subjected to a condensation reaction; a dehydration reaction and a reduction reaction are carried out to obtain leonurus amine; and the leonurus amine and S-methyl isothiourea sulfate are subjected to a reaction to obtain the leonurine. The target product leonurine is synthetized from the cheap industrial raw materials of the gamma-butyrolactone and the syringic acid used as the starting materials through reactions of ammonolysis, esterification, dehydration, reduction and the like. The reaction conditions are mild and easy to control; the yield is up to 65%; the product purity is 98% or above; and the synthetic method for leonutine provides the production with an excellent synthetic route and is suitable for large-scale production.

Description

technical field [0001] The invention belongs to the technical field of organic chemistry, and relates to a method for synthesizing a compound, in particular to a method for synthesizing leonurine. Background technique [0002] Motherwort is the dry aerial part of LeunornsheterophyLLus Sweet, a plant of the Labiatae family. It is a traditional Chinese medicine species recorded in the Chinese Pharmacopoeia. It has the functions of regulating menstruation, promoting blood circulation and relieving pain. In recent years, relevant clinical experiments have also proved that it has a significant effect on the treatment of cardiovascular diseases. [0003] Through the research, it is found that the reports on several synthetic methods of Leonurine all have defects of different degrees of process expansion, such as: Zhu Renfa, Wang Xiaoshan, etc., use the Gabriel method and the reduction of hydrazine to prepare Leonurine. During the experiment Due to problems such as the poor solubi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C277/08C07C279/08C07C213/02C07C219/14C07C253/20C07C255/14C07C231/12C07C235/06C07C67/08C07C69/157C07C231/02
CPCC07C67/08C07C213/02C07C231/02C07C231/12C07C253/20C07C277/08C07C279/08C07C219/14C07C255/14C07C235/06C07C69/157
Inventor 张永
Owner 绵阳市润土农业科技开发有限公司
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