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A kind of preparation method of four-membered ring taxane side chain compound

A compound and taxane technology, applied in the field of preparation of four-membered ring taxane side chain compounds, can solve the problems of unsuitability for industrial production, low reaction yield, cumbersome post-treatment, etc., and achieve easy industrial production and harvest The effect of high efficiency and simple equipment

Active Publication Date: 2017-10-31
无锡紫杉药业股份有限公司
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  • Abstract
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  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0002] The prior art discloses a variety of preparation methods for four-membered ring taxane side chain compounds. The basic scheme is to use hydroxyl-protected (2R,3S)-phenylisoserine methyl ester as a starting material, and in the presence of an organic base , a cyclization reaction occurs under low temperature conditions to obtain a four-membered ring side chain, but the reaction yield is not high, and the post-treatment is cumbersome, requiring column chromatography to obtain a purified product, which is not suitable for industrial production

Method used

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  • A kind of preparation method of four-membered ring taxane side chain compound
  • A kind of preparation method of four-membered ring taxane side chain compound
  • A kind of preparation method of four-membered ring taxane side chain compound

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0023] The compound shown by formula II (2mmol) and lithium chloride (0.2mmol) were dissolved in tetrahydrofuran (20mL) respectively, put into an ice-water bath, and after cooling to -30°C, lithium hexamethyldiaminesilyl ( 2mmol), after reacting for 1 hour, TLC showed that the raw materials were completely reacted, the reaction solution was poured into a saturated ammonium chloride aqueous solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, suction filtered and concentrated to obtain a crude product. The crude product is crystallized with sherwood oil / ethyl acetate to obtain the refined product, and the yield is 34%. figure 1 shown.

[0024] The control of the reaction temperature in this embodiment is completed under the protection of nitrogen; in addition, the catalyst—lithium chloride can also be added simultaneously with the base—hexamethyldiaminosilyllithium.

[0025] 1H-NMR (400MHz, d6-DMSO): 0.44 (m, 6H); 0.76 (t, J = 7.9, 9H); 4.79 (d, J = 4.7...

Embodiment 2

[0028] The compound shown by formula II (2mmol) and lithium chloride (1.8mmol) were added to tetrahydrofuran (20mL) to dissolve respectively. At 25°C, lithium hexamethyldiamide silicon base (20mmol) was added, and after 8 hours of reaction, TLC It showed that the reaction of raw materials was complete, the reaction solution was poured into saturated ammonium chloride aqueous solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, filtered with suction and concentrated to obtain a crude product. The crude product is crystallized with sherwood oil / ethyl acetate to obtain the refined product, and the yield is 45%. figure 1 shown.

[0029] The control of the reaction temperature in this embodiment is completed under the protection of nitrogen; in addition, the catalyst—lithium chloride can also be added simultaneously with the base—hexamethyldiaminosilyllithium.

[0030]

Embodiment 3

[0032] The compound shown by formula II (2mmol) and lithium chloride (0.4mmol) were added to tetrahydrofuran (20mL) to dissolve respectively, put into an ice-water bath, and after cooling to 0°C, hexamethyldiaminosilyllithium (8mmol ), after reacting for 4 hours, TLC showed that the raw material had reacted completely, and the reaction solution was poured into a saturated ammonium chloride aqueous solution, extracted with ethyl acetate, dried over anhydrous sodium sulfate, suction filtered and concentrated to obtain a crude product. The crude product is crystallized with petroleum ether / ethyl acetate to obtain a refined product, and the yield is 91%. figure 1 shown.

[0033] The control of the reaction temperature in this embodiment is completed under the protection of nitrogen; in addition, the catalyst—lithium chloride can also be added simultaneously with the base—hexamethyldiaminosilyllithium.

[0034]

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Abstract

The invention relates to a preparation method of a quaternary ring taxane side chain compound, which belongs to the field of pharmaceutical synthesis. produced by chemical reaction. The preparation method overcomes the defects of the prior art that the reaction yield is not high, the post-processing is cumbersome, and the purified product needs to be obtained by column chromatography, and the required equipment is simple, easy to operate, high yield, and easy to industrialize. The advantages of production.

Description

technical field [0001] The invention relates to a preparation method of a four-membered ring taxane side chain compound, belonging to the field of drug synthesis. Background technique [0002] The prior art discloses a variety of preparation methods of four-membered ring taxane side chain compounds. The basic scheme is to use hydroxyl-protected (2R,3S)-phenylisoserine methyl ester as a starting material, and in the presence of an organic base , Under low temperature conditions, a cyclization reaction occurs to obtain a four-membered ring side chain, but the reaction yield is not high, and the post-treatment is cumbersome, requiring column chromatography to obtain a purified product, which is not suitable for industrial production. Contents of the invention [0003] The technical problem to be solved by the present invention is to provide an easy-to-operate, high-yield preparation method of a four-membered ring taxane side chain compound in view of the current state of the ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18
Inventor 陈磊葛月兰
Owner 无锡紫杉药业股份有限公司
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