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Preparation method for green synthesis of tanshinone IIA sodium sulfonate

A technology of green synthesis and tanshinone, which is applied in the field of medicine, can solve the problems of harsh reaction conditions, reagent stability, poor safety, and difficult recovery of pyridine sulfur trioxide, and achieve safe and controllable reaction process, safe reaction reagents, and short production cycle. shortened effect

Active Publication Date: 2019-07-09
SHANGHAI XINGYE PHARM TECH CO LTD
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AI Technical Summary

Problems solved by technology

[0004] Yet the synthetic method of existing sodium tanshinone IIA sulfonate mainly adopts the method for the sulfonation of concentrated sulfuric acid, and reagents such as a large amount of acetic acid, acid anhydride, saturated saline used during the period are also difficult to reclaim because of the inherent defect of the synthetic method, and in the production process A large amount of waste gas such as hydrochloric acid is also produced in the process, which not only brings great safety hazards to production, but also creates great pressure on the development of the environment; The sulfonation reaction of sulfur trioxide compound on tanshinone IIA (CN201310669822.4). Although this synthesis method avoids the use of corrosive reagents such as concentrated sulfuric acid and acetic acid, it also introduces a large amount of polluting organic solvents and still needs to be processed. Saturated sodium carbonate and sodium bicarbonate solutions, and pyridine sulfur trioxide acidification reaction conditions are harsh (no water required), reagent stability and safety are poor, which also poses great challenges to production and the environment

Method used

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  • Preparation method for green synthesis of tanshinone IIA sodium sulfonate
  • Preparation method for green synthesis of tanshinone IIA sodium sulfonate
  • Preparation method for green synthesis of tanshinone IIA sodium sulfonate

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1 Cu(OAc) 2 Catalytic Synthesis and Preparation of Sodium Tanshinone IIA Sulfonate

[0048] Tanshinone IIA (2.94 g, 10 mmol) was dissolved in 50 ml of acetic anhydride solution containing sodium bisulfate (1.44 g, 12 mmol); then 10 mol% of the catalyst Cu(OAc) was added 2 (0.18 g, 1 mmol), and at 60 o C is heated until the reaction is complete. After the TLC detection reaction was completed, the anhydride solution of the reaction system was recovered under reduced pressure, and the remaining red solid was added to 100 ml ethanol solution, and the insoluble matter was filtered off; Standing and crystallizing overnight; filtering to obtain 3.67 g of tanshinone IIA sodium sulfonate crystals, with a yield of 92.7% and a content of 99%. Correlation spectrum data of sodium tanshinone IIA sulfonate: HRMS (ESI): [M+Na] + m / z: 396.0647. UV (MeOH) λmax (nm): 202, 226, 225, 271, 279. IR (KBr) (cm -1 ): 3000~2840, 1695, 1674, 1576, 1539, 1459, 1245, 1217, 1041, 923,...

Embodiment 2

[0049] Example 2 Synthesis and preparation of Tanshinone IIA sodium sulfonate catalyzed by aza-15-crown ether-5

[0050] Tanshinone IIA (2.94 g, 10 mmol) was dissolved in 30 ml of acetic anhydride solution containing sodium bisulfate (1.44 g, 12 mmol); then 10 mol% of the catalyst aza-15-crown-5 (0.11 g, 0.5 mmol), and reacted at room temperature for 1 hour to complete. After the TLC detection reaction was completed, dichloromethane was added until a large amount of red solids were precipitated, allowed to cool and then filtered, and the gained red solids were added to 100 ml of ethanol-methanol mixed solution (V 乙醇 :V 甲醇 = 4:1), filtered to remove insoluble matter; the obtained filtrate was concentrated until a small amount of solid precipitated, left to stand, and continued to crystallize overnight at room temperature; filtered to obtain 3.80 g of tanshinone IIA sodium sulfonate crystals, with a yield of 96%. The content is 98%. Related spectral data of sodium tanshinone ...

Embodiment 3

[0051] Example 3 Recovery of acetic anhydride for the synthesis and preparation of tanshinone IIA sodium sulfonate

[0052] The dichloromethane / acetic anhydride filtrate used in the reaction of Example 2 was concentrated under reduced pressure to recover dichloromethane, and then Tanshinone IIA (2.94 g, 10 mmol) and sodium bisulfate (1.44 g, 12 mmol) and 10 mol% catalyst Cu(OAc) 2 (0.18 g, 1 mmol), and at 80 o C is heated until the reaction is complete. After the reaction was detected by TLC, according to the post-treatment method of Example 2, 3.60 g of tanshinone IIA sodium sulfonate crystals were obtained, with a yield of 91% and a content of 99%. Related spectral data of sodium tanshinone IIA sulfonate: 1 H NMR (500MHz, DMSO- d 6 , TMS) δ ppm : 7.85 (1H, d, J = 8.4 Hz,H-6), 7.57 (1H, d, J = 8.4 Hz, H-7), 3.08 (2H, t, J = 6.1 Hz, H-1), 2.33 (3H, s, 17-CH 3 ), 1.72 (2H, m, H-2), 1.62 (2H, m, H-3), 1.29 (6H, s, 18,19-CH 3 ).

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Abstract

The invention discloses a novel green synthesis method of tanshinone IIA sodium sulfonate, which comprises the following step: directly carrying out a sulfonation reaction on tanshinone IIA by adopting safe, stable and cheap sodium hydrogen sulfate in the presence of a catalyst to obtain tanshinone IIA sodium sulfonate. Compared with the existing method, the method has the advantages that a targetproduct can be obtained through a one-step reaction; strong corrosive sulfonation reagents such as concentrated sulfuric acid and pyridine sulfur trioxide and a large amount of saturated salt water and sodium carbonate needed by subsequent salt forming are avoided. The method has the advantages that the production process is simple and convenient, the efficiency is high, and reagents can be recycled, so that the production cost of the tanshinone IIA sodium sulfonate is obviously reduced, the environmental pollution pressure is greatly relieved, and the method has a great industrial productionvalue.

Description

technical field [0001] The invention belongs to the technical field of medicines, and in particular relates to a green method for synthesizing sodium tanshinone IIA sulfonate. Background technique [0002] Sodium tanshinone IIA sulfonate is the sulfonated product of tanshinone IIA, a fat-soluble active ingredient of traditional Chinese medicine for promoting blood circulation and removing blood stasis. Protecting cardiomyocytes, increasing coronary artery flow, anti-oxidation, anti-myocardial ischemia and other pharmacological activities, which have been developed into injection drugs (Nuoxinkang, Shanghai No. 1 Biochemical) and widely used clinically for coronary heart disease, angina pectoris, myocardial infarction Treatment of cardiovascular and cerebrovascular diseases. With the aggravation of my country's population aging trend, the incidence of cardiovascular and cerebrovascular diseases remains high, and the market demand for this drug also shows a trend of increasin...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J73/00
CPCC07J73/003
Inventor 王大千于汶君穆静魏珩鞠知文宋艳萍其他发明人请求不公开姓名
Owner SHANGHAI XINGYE PHARM TECH CO LTD
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