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Desogestrel intermediate and preparation method thereof

A technology for desogestrel and intermediates, which is applied in the field of desogestrel intermediate compounds and their preparation, and can solve the problems of poor selectivity of the 17-position carbonyl group, unsuitability for industrial production, and high cost, so as to achieve reduced electron density and easy operation , the effect of high yield

Inactive Publication Date: 2019-02-26
CHINA RESOURCES ZIZHU PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] In this reaction route, when compound 4 is synthesized from compound 3, the 17-position carbonyl is selectively protected. According to the description in the document US5831104, this step has poor selectivity to the 17-position carbonyl, resulting in high cost, so it is not suitable for industrial production.

Method used

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  • Desogestrel intermediate and preparation method thereof
  • Desogestrel intermediate and preparation method thereof
  • Desogestrel intermediate and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0049] Embodiment 1: the preparation of compound II (tert-butoxy)

[0050] Add compound I (150g, 0.5mol) into a 3000mL three-neck flask, measure 1500mL of dichloromethane into the three-necked flask, and stir to dissolve. Add 210 mL of pyridine, pivaloyl chloride (120 g, 1 mol) and 1.5 g of DMAP, raise the temperature to 40 ° C, start to reflux, and stir for about 8 hours; after TLC monitors that the reaction is complete, add an appropriate amount of prepared sodium hydroxide solution, adjust the pH to be alkaline, Add 300mL of drinking water and stir, then pour into the separatory funnel, separate the organic phase and add the prepared saturated ammonium chloride aqueous solution, measure the pH of the aqueous phase to 7, separate the organic phase, add the prepared saturated sodium chloride aqueous solution, separate the organic phase Add 20g of anhydrous magnesium sulfate to dry for 30min, filter with suction, and concentrate the filtrate under reduced pressure at P=-0.08Mp...

Embodiment 2

[0052] Embodiment 2: the preparation of compound II (chloro group)

[0053] Take compound I (250g, 0.8mol) and add it into a 5000mL three-necked flask, measure 2500mL of dichloromethane into the three-necked flask, and stir to dissolve. Add 350mL of pyridine, trichloroacetyl chloride (288g, 1.6mol) and 2.5g of DMAP, raise the temperature to 40°C, start to reflux, and stir the reaction for about 8h; after TLC monitors that the reaction is complete, add an appropriate amount of prepared sodium hydroxide solution, and adjust the pH to alkali Add 400mL of drinking water, stir and pour into a separatory funnel, separate the organic phase and add the prepared saturated ammonium chloride aqueous solution, measure the pH of the aqueous phase to 7, separate the organic phase and add the prepared saturated sodium chloride aqueous solution, separate The organic phase was dried by adding 20 g of anhydrous magnesium sulfate for 30 min, filtered with suction, and the filtrate was concentrat...

Embodiment 3

[0055] Embodiment 3: the synthesis of compound III (tert-butoxy)

[0056] The compound (190 g) prepared in Example 1 was weighed and added into a 3000 mL three-necked flask, and 1900 mL of tetrahydrofuran was weighed and added into the three-necked flask, and stirred to dissolve. The reaction flask was evacuated three times, and 290 g of hydrogen peroxide was slowly added into the three-necked flask in batches of 3-5 under the protection of argon, and the temperature was slowly raised to 60°C, and the reaction was stirred for 2-4 hours. After the completion of the reaction was monitored by TLC, the temperature was lowered to 25.±5°C, and the prepared sodium thiosulfate solution was added and stirred for 30 minutes. Pour the reaction solution into a separatory funnel and let it stand, add 400mL ethyl acetate to the aqueous phase to extract once, combine the organic phase and add the prepared sodium chloride aqueous solution to extract once, combine the organic phase, at P=-0.08...

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Abstract

The invention relates to a steroid compound, i.e., a desogestrel intermediate (a compound VI), and a preparation method thereof. According to the method, 13beta-ethyl-3-methoxy-estra-1,3,5(10),8(9)-tetraen-17beta-ol is uses as a starting material and subjected to protection, epoxidation, hydrolysis, epoxidation and hydrolysis to produce the target product. The route of the method is simple and easy; chemical reagents used in the method are relatively economical and environmentally-friendly; and the method is simple in process, high in yield and suitable for industrial production. In the formula VI which is described in the specification, R is A and -CH3, or B and -Cl.

Description

technical field [0001] The invention belongs to the technical field of medicinal chemistry. It specifically relates to a desogestrel intermediate compound and a preparation method thereof. technical background [0002] Desogestrel is a powerful oral progestogen, and its progesterone activity is 18 times stronger than norethindrone and 1 times stronger than norethindrone. And no androgenic and estrogenic activity. When the drug is used for contraception, the effect is reliable and the safety is good, and it is widely used clinically. [0003] There are many synthetic methods of desogestrel at home and abroad. Chinese patent CN201510995906.6 discloses a preparation method of desogestrel intermediate, which uses D-13β-ethyl-3-methoxy-estradiol-1,3, 5(10), 8(9)-tetraen-17β-alcohol I was used as raw material, and compound II was obtained through the protection of the 17-hydroxyl group; the 8,9-position double bond was converted into the 9,11-position double bond in an acidic m...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
CPCC07J1/0066C07J1/0074
Inventor 梁佶轩唐四华杨龙宋晓亮张冲李振龙邓强孙玉霞耿聪聪
Owner CHINA RESOURCES ZIZHU PHARMA
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