Pterostilbene phosphate disodium salt synthesis method

A technology of pterostilbene phosphate disodium salt and pterostilbene phosphate, which is applied in the field of synthesis of water-soluble pterostilbene derivative pterostilbene phosphate disodium salt, can solve the problems of difficult quality control, many reaction by-products, and product yield. Low-level problems, to achieve the effect of short response time, simple operation and good quality

Active Publication Date: 2013-11-27
ZHANG JIA GANG VINSCE BIO PHARM
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

Although the method is simple to operate, the activity of phosphorus oxychloride or phosphorus oxypimanide is high, so there are many reaction by-products, the yield of finished product is low and the quality is difficult to control

Method used

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  • Pterostilbene phosphate disodium salt synthesis method

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Comparison scheme
Effect test

Embodiment 1

[0026] Under nitrogen protection, 2.56 g (0.01 mol) of pterostilbene, 0.06 g (0.0005 mol) of 4-dimethylaminopyridine and 1.42 g (0.011 mol) of diisopropylethylamine were dissolved in 20 ml of dichloromethane, at 20 °C, a solution of 2.51 g (0.011 mol) of di-(tert-butoxy)-phosphoryl chloride and 10 ml of dichloromethane was added dropwise. After the dropwise addition, keep the temperature and stir the reaction, monitor the reaction process with thin-layer chromatography, until the raw material point disappears, the reaction time is 0.5 hour, the reaction solution is poured into 50ml ice water, the organic layer is separated, and the water layer is refilled with 20ml diethyl alcohol. Extract once with methyl chloride, combine the organic layers, wash with water, dry, and evaporate to dryness to obtain a yield of 94% oil pterostilbene-di-(tert-butoxy)-phosphate 4.07g, and put it into 50ml of pre-dried hydrogen chloride into saturated methanol, stirred at room temperature for 24 h...

Embodiment 2

[0028] Under nitrogen protection, dissolve pterostilbene 2.56g (0.01moi), 4-dimethylaminopyridine 0.06g (0.0005mol) and diisopropylethylamine 1.428 (0.011mol) in 20ml of dichloromethane, at 30°C A solution of 2.45 g (0.011 mol) of bis-(2-cyanoethoxy)-phosphoryl chloride and 10 ml of dichloromethane was added dropwise. After the dropwise addition is completed, keep the temperature and stir the reaction, monitor the reaction process with thin layer chromatography, until the raw material point disappears, the reaction time is 0.8 hours, the reaction solution is poured into 50ml of ice water, the organic layer is separated, and the water layer is re-used with 20ml of two Methyl chloride was extracted once, the organic layers were combined, washed with water, dried, and evaporated to dryness to obtain a yield of 93% oil pterostilbene-bis-(2-cyanoethoxy)-phosphate 4.45g, which was dropped into 25ml of methanol, Add NaOH-methanol solution dropwise under stirring until the pH is 8-10,...

Embodiment 3

[0030] Under nitrogen protection, dissolve pterostilbene 2.56g (0.01mol), 4-dimethylaminopyridine 0.068 (0.0005mol) and diisopropylethylamine 1.42g (0.011mol) in 20ml of chloroform, at 20°C A solution of 6.61 g (0.011 mol) of bis-(triphenylmethoxy)-phosphoryl chloride and 10 ml of chloroform was added dropwise. After the dropwise addition is completed, keep the temperature and stir the reaction, monitor the reaction process with thin layer chromatography, until the raw material point disappears, the reaction time is 0.5 hour, the reaction solution is poured into 50ml ice water, separate the organic layer, and the water layer is washed with 20ml three Chloromethane was extracted once, and the organic layers were combined, washed with water, dried, and evaporated to dryness to obtain a yield of 89% oil pterostilbene-bis-(triphenylmethoxy)-phosphate 7.92g, and put it into 50ml that had been passed through in advance. Dry hydrogen chloride into saturated methanol, stir at room tem...

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Abstract

The present invention provides a pterostilbene phosphate disodium salt synthesis method, wherein an aprotic solvent is adopted to dissolve pterostilbene, a dialkoxyl phosphoryl halide is adopted as a phosphorylation regent, acylation is performed under catalysis effects of an acid removing agent and 4-dimethylaminopyridine to obtain pterostilbene-alkoxyl-phosphate ester, and hydrolysis, salt formation and crystallization are performed to obtain the pterostilbene phosphate disodium salt. The method has characteristics of mild reaction conditions, short reaction time, no requirement of purification of the phosphorylation intermediate, simple process, high yield, good product quality and low energy consumption, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a synthesis method of water-soluble pterostilbene derivative pterostilbene phosphate disodium salt, belonging to the technical field of chemical medicine preparation. Background technique [0002] Pterostilbene (Pterostilbene), also known as pterostilbene, chemical name 3,5-dimethoxy-4'-hydroxystilbene, CAS NO.537-42-8, molecular formula C 16 h 16 o 3 , the molecular weight is 256.30. Off-white crystalline powder, insoluble in water, soluble in ethanol, sensitive to air, melting point is 89-92°C. Pterostilbene is a homologue of resveratrol, which has a trans-stilbene skeleton structure. It is an important active ingredient in grapes, blueberries, dried blood products and Indian anti-diabetic herbal medicine "Bijasar". It also exists in Chinese herbal medicine, and its pharmacological effects are partially similar to those of resveratrol. It is a good antioxidant and has many activities such as anti-inflammation, anti-thromb...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07F9/12
Inventor 彭学东张梅赵金召弓旻
Owner ZHANG JIA GANG VINSCE BIO PHARM
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