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The method for preparing uliplast acetate bisketal

A technology of uliplast acetate and bisketal, which is applied in the direction of ketal steroids, chemical instruments and methods, and steroidal compounds, can solve the problems of single starting raw materials, high cost of raw and auxiliary materials, and large safety hazards, and achieve Increased yield, increased synthesis efficiency, and reduced production costs

Active Publication Date: 2020-01-07
台州仙琚药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0016] The purpose of the present invention is to solve the technical problems of single starting raw material, high cost of raw and auxiliary materials, high toxicity and great potential safety hazard in the current synthetic process of uliplast acetate bisketal

Method used

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  • The method for preparing uliplast acetate bisketal
  • The method for preparing uliplast acetate bisketal
  • The method for preparing uliplast acetate bisketal

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0059] The first step, ketal reaction: dihydroxyprogesterone dehydrogenate 1 (10g, 1W), ethylene glycol (14ml, 1.4V), triethyl orthoformate (9ml, 0.9V) were dissolved in dichloromethane ( 20ml, 2V), stirred and reacted at 20-25°C, added p-toluenesulfonic acid (0.2g, 0.02W), stirred and reacted at 20-25°C for 2 hours, TLC detected no raw material point, stopped the reaction, and used triethyl The amine was used to adjust the pH to 8, and the solvent was removed by rotary evaporation under reduced pressure, poured into 100ml of ice water for precipitation, stirred, filtered with suction, and dried at 65°C to obtain ketal 2 (11g, 110%), HPLC (240nm, 98 %).

[0060] The second step, aromatic hydrolysis reaction: put benzophenone (15.4g, 1.4W) and ethoxymethane (50.6ml, 4.6V) into the reaction flask to stir, blow nitrogen, cool down to 5-15°C, Add Lithium (5.5g, 0.5W), keep warm at 40-50°C for 0.5 hours, add ketal 2 (11g, 1W) diethoxymethane (22ml, 2V) dropwise, and stir at 80-88°...

Embodiment 2

[0067] The second step, aromatic hydrolysis reaction: put benzophenone (20g, 2W) and tetrahydrofuran (90ml, 9V) into the reaction bottle to stir, blow nitrogen, cool down to 5-15°C, put lithium (12g, 1.2W ), insulated and reacted at 40-50°C for 0.5 hours, added dropwise a solution of ketal 2 (10g, 1W) tetrahydrofuran (20ml, 2V), stirred and reacted at 60-66°C for 2 hours, no raw material point was detected by TLC, and cooled to Stir and add methanol (126ml, 12.6V) dropwise at 15-30°C, then add dropwise 50% dilute hydrochloric acid (concentrated hydrochloric acid (50ml, 5V) + water (50ml, 5V)), heat up to reflux and stir for 2 hours, depressurize Remove the solvent by rotary evaporation, filter with suction, wash the filter cake with hot water above 50°C, wash with ethanol (10ml, 1V), and dry at 60°C to obtain aromatic hydrolyzate 3 (7.5g, 75%), HPLC (240nm, 93%).

[0068] Other steps are with embodiment 1.

Embodiment 3

[0070] The second step, aromatic hydrolysis reaction: put benzophenone (14g, 1.2W) and dimethyltetrahydrofuran (52ml, 5.2V) into the reaction bottle to stir, blow nitrogen, cool down to 5-15°C, and put in lithium (5g, 0.4W), keep warm at 40-50°C for 1 hour, add dropwise ketal 2 (10g, 1W) dimethyltetrahydrofuran (20ml, 2V) solution, stir and react at 80-90°C for 3 hours, TLC detects that there is no raw material point, and the temperature is lowered to 15 to 30°C, and methanol (76ml, 7.6V) is added dropwise with stirring, and then 50% dilute hydrochloric acid (concentrated hydrochloric acid (42ml, 4.2V)+water (42ml, 4.2V)) is added dropwise, Raise the temperature to reflux and stir the reaction for 2 hours, remove the solvent by rotary evaporation under reduced pressure, filter with suction, wash the filter cake with hot water above 50°C, wash with ethanol (10ml, 1V), and dry at 60°C to obtain the aromatic hydrolyzate 3 (7.0 g, 70%), HPLC (240nm, 90%).

[0071] Other steps are...

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Abstract

The invention discloses a preparation method of ulipristal acetate diketal. Dihydroxyprogesterone dehydrogenate 1 is used as the raw material to prepare an important intermediate of sterides, namely ulipristal acetate diketal 8; a reaction formula is shown in the attached figure. The preparation method has the advantages that the dihydroxyprogesterone dehydrogenate 1 is used as a starting raw material, seven steps are performed, and the ulipristal acetate diketal with weight total yield rate of 65% or above can be obtained; the reaction is simple, the selectivity is good, and the preparation method is suitable for industrialization production.

Description

technical field [0001] The invention relates to a method for preparing chemicals, in particular to a method for preparing uliplast acetate bisketal. Background technique [0002] Ulipristal Acetate is a progesterone agonist / antagonist whose main function is to inhibit or delay ovulation. Uliplast acetate has a good effect in the short-term treatment of uterine fibroids, controlling bleeding, reducing the size of fibroids and improving pain. Uliplast acetate bisketal is an important intermediate for the synthesis of Uliplast acetate. [0003] The CAS number of bisketal is 54201-84-2, and its structural formula is: [0004] [0005] According to relevant reports, the technical routes for preparing Ulix acetate bisketal are roughly as follows: [0006] 1. U.S. Patent US4954490 discloses a preparation method of Uliplast acetate, which includes the preparation of Uliplast acetate bisketal, and 3-methoxy-19-norpregna-1,3,5 (10), 17(20)-Tetraene as the starting material, thr...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J21/00
CPCC07J21/006
Inventor 许宏顾光志戴静
Owner 台州仙琚药业有限公司
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