Conversion 9-dihydro-13-acetylbaccatin iii to 10-deacetylbaccatin iii

A technology of acetylbaccatin and deacetylbaccatin, applied in the direction of organic chemistry, etc., can solve the problem of low yield of the target product

Inactive Publication Date: 2007-09-12
6570763 CANADA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0010] However, as pointed out above, many proposed methods for converting 9-dihydro-13-acetylbaccatin III into 10-deacetylbaccatin III have low yields of the desired product.

Method used

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  • Conversion 9-dihydro-13-acetylbaccatin iii to 10-deacetylbaccatin iii

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Embodiment

[0026] Conversion of 9-dihydro-13-acetylbaccatin III to 10-deacetylbaccatin III

[0027] 1. Purification of crude product 9-dihydro-13-acetylbaccatin III (9-DHA)

[0028] Put the crude 9-DHA (9-dihydro-13-acetylbaccatin III) into a round bottom flask, add 5-10 times methanol, and reflux the mixture for 1 hour or until all the 9-DHA is completely dissolved Afterwards, some methanol-insoluble yellow solid was removed by filtration. The supernatant was concentrated to remove most of the solvent and left at room temperature overnight. The resulting white crystals were filtered out, and the needle-shaped crystals were dried in an oven at 80-100° C. to obtain white needle-shaped 9-DHA with a purity greater than 98%.

[0029] 2. 9-DHA protection

[0030] Choose one of the methods

[0031] 2.1: 10g 9-DHA was dissolved in 100ml dichloromethane, stirred at room temperature for 5 minutes, then added 1.5mol tetrabutylammonium iodide and 5mol acetyl chloride, and the mixture was stirre...

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Abstract

The present invention relates to a process is provided for the conversion of 9-dihydro-13-acetylbaccatin to 10-deacetylbaccatin III. The process includes four specific interrelated steps. The first step involves protecting the 7-hydroxyl group of 9-dihydro-13-acetylbaccatin and converting that 7-hydroxyl-protected 9-dihydro-13-acetylbaccatin to 7, 13-diacetyl-9-dihydrobaccatin III. The second step involves reacting that 7, 13-diacetyl-9-dihydrobaccatin III with 4-methylmorpholine N-oxide in a suitable solvent and oxidizing that reaction product to yield 7, 13-diacetylbaccatin. The third step involves deacetylating that 7, 13-diacetyl-9-dihydrobaccatin III to yield 7-acetylbaccatin III. The fourth and final step involves converting that 7-acetylbaccatin III to 10-deacetylbaccatin III.

Description

technical field [0001] The present invention relates to a method for converting 9-dihydro-13-acetyl baccatin III into 10-deacetyl baccatin III. Background technique [0002] Paclitaxel (paclitaxel) is a potent antineoplastic substance that prevents the growth of cancer cells by a unique mechanism affecting microtubules, which play an important role in cell division and other cellular functions. When cell division begins, a large number of microtubules are formed, and when division is terminated, the microtubules are usually destroyed. Paclitaxel can prevent the destruction of microtubules, thereby hindering the growth and division of cancer cells. [0003] Paclitaxel can effectively treat refractory human ovarian cancer and breast cancer clinically. In addition, it is also a promising drug for some other cancers, such as cancers such as liver, peritoneum, neck, prostate, colon, and esophagus. active. [0004] Paclitaxel was originally extracted from the bark of the Pacifi...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D305/14
CPCC07D305/14
Inventor 刘健
Owner 6570763 CANADA
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