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A kind of new intermediate for preparing prostaglandin and its preparation method and application

A technology for prostaglandin and alprostadil, which is applied in chemical instruments and methods, compounds of periodic table Group 4/14 elements, and production of bulk chemicals, etc., can solve the problems of complicated preparation process, low yield, long time consumption, etc.

Active Publication Date: 2018-04-24
CHANGZHOU BOHIV PHARM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The synthesis process of the intermediate (2R,3R)-1,2-epoxypent-4-en-3-ol requires a continuous reaction at a low temperature of -20°C for 90 hours, the conditions are complex, time-consuming, and the yield is low
Intermediate VII needs to be synthesized in ten steps, and the synthesis process is cumbersome
[0008] Therefore, the intermediate VI synthesized by this synthetic method affects its application in the synthesis of prostaglandins because of its complicated preparation process

Method used

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  • A kind of new intermediate for preparing prostaglandin and its preparation method and application
  • A kind of new intermediate for preparing prostaglandin and its preparation method and application
  • A kind of new intermediate for preparing prostaglandin and its preparation method and application

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preparation example Construction

[0052] In a specific embodiment, the preparation method of the compound represented by formula VI comprises: dissolving the compound represented by S-I or R-I in dichloromethane, adding an oxidizing agent, and stirring at room temperature until the reaction is complete. After treatment, the compound shown in formula IV is obtained. After the compound represented by formula IV is dissolved in acetone, sodium bromide is added to catalyze bromination with boron trifluoride ether to obtain the compound represented by formula V. The compound shown in formula V reacts with diethylamine in the presence of triethylamine to obtain the compound shown in formula VI.

[0053] In the above reaction, the oxidizing reagent can be selected from IBX, Dess-Martin reagent, PDC. Among them, the PDC oxidation reaction is used, and the post-treatment is relatively cumbersome, and diatomaceous earth is required for filtration. The oxidation effect of Dess-Martin reagent is good, but the stability ...

Embodiment 1

[0060] The preparation of embodiment 1.S-I (R 1 = tert-butyldimethylsilyl)

[0061]

[0062] Compound (S,S)-II (38.8g, 0.1mol) was dissolved in dichloromethane (582.0ml), diacetyliodobenzene (22.6g, 0.07mol) was added, and stirred to dissolve. Under the light, iodine (12.7 g, 0.05 mol) was added in batches, and the reaction solution was stirred from reddish brown until the color disappeared, indicating that the reaction was complete. Post-treatment: Pour the reaction solution into an aqueous solution containing saturated sodium sulfite / sodium bicarbonate, and stir until the KI test paper does not turn blue. The layers were separated, and the aqueous layer was back-extracted with dichloromethane. The organic layers were combined, washed twice with water and once with saturated brine, and separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain an oil. The oil was dissolved in acet...

Embodiment 2

[0065] The preparation of embodiment 2.S-I (R 1 = trimethylsilyl)

[0066]

[0067] Compound (S,S)-II (27.6g, 0.1mol) was dissolved in dichloromethane (582.0ml), diacetyliodobenzene (22.6g, 0.07mol) was added, and stirred to dissolve. Under the light, iodine (12.7 g, 0.05 mol) was added in batches, and the reaction liquid was stirred from reddish brown until the color disappeared, and the reaction was complete. Post-treatment: Pour the reaction solution into an aqueous solution containing saturated sodium sulfite / sodium bicarbonate, and stir until the KI test paper does not turn blue. The layers were separated, and the aqueous layer was back-extracted with dichloromethane. The organic layers were combined, washed twice with water and once with saturated brine, and separated. The organic layer was dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to obtain an oil. The oil was dissolved in acetonitrile (582.0ml), and...

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Abstract

The present invention provides a compound represented by formula S-I or R-I with a completely new structure and a preparation method of the compound. The compound of the present invention can be used to prepare prostaglandin key intermediates and derivatives thereof; the method of the present invention is applicable to the key intermediates in the 1,4-addition synthesis route of prostaglandins, can greatly shorten the synthetic steps of prostaglandins, improve Synthetic efficiency and reduced production costs.

Description

technical field [0001] The present invention relates to the field of chemical synthesis. Specifically, the present invention relates to a novel intermediate for the preparation of prostaglandins, a preparation method of the intermediate and an application of the intermediate in the preparation of prostaglandins. Background technique [0002] Prostaglandins (PG) are a class of important endogenous natural products with multiple biological activities. They play an important role in the reproductive system, respiratory system, digestive system and cardiovascular system. It can cause the body's defense reactions such as inflammation and pain, and can regulate physiological and pathological processes such as pregnancy, hypertension, ulcers, asthma, glaucoma and pain, and is an important mediator of various physiological processes. [0003] The 1,4-addition synthetic route of prostaglandin (Alprostadil, alprostadil) is as follows: [0004] [0005] The synthetic method of the...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18C07D309/12C07C405/00
CPCY02P20/55
Inventor 刘向群李强陈宣福
Owner CHANGZHOU BOHIV PHARM TECH CO LTD
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