Synthetic method of 6-methyl-17alpha-acetoxyl-19-norpregna-4,6-dialkyl-3,20-diketone

A technology of acetoxy and methylpregnant, applied in the field of compound synthesis, can solve problems such as difficulty in obtaining, and achieve the effects of simplified operation, simple reaction operation and high yield

Active Publication Date: 2013-03-06
黄云生 +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, this starting material is very difficult to obtain. At home and abroad, it mainly relies on the semi-synthesis of tuber plant resources, and a total of 15 steps of reaction

Method used

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  • Synthetic method of 6-methyl-17alpha-acetoxyl-19-norpregna-4,6-dialkyl-3,20-diketone
  • Synthetic method of 6-methyl-17alpha-acetoxyl-19-norpregna-4,6-dialkyl-3,20-diketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] 1.1, 19-desmethyl-21-phenylsulfinylpregna-4,17(20),20-triene (2)

[0028] Add compound 1 (17α-ethynyl-17β-hydroxy-19-normethylpregn-4-en-3-one) (10 g, 33.5 mmol), dichloromethane (500 ml), triethylamine into the reaction flask (17g, 167.5mmol), cooled in an ice bath below -10°C, added dropwise a dichloromethane solution (25ml) of benzenesulfenyl chloride (9.68g, 67mmol), reacted at -10°C for 20 minutes, added water (150ml) and Methanol (30ml), stirred and separated, washed with dilute hydrochloric acid and saturated NaCl solution, dried, concentrated the solvent, recrystallized to obtain a white solid product, dried and weighed 11.4g, yield 85%. HNMR (ppm, CDCl 3 ): 7.63-7.66(m,2H),7.46-7.55(m,3H),6.11-6.15(m,1H),5.83(s,1H),2.65-2.71(m,1H),2.47-2.58(m ,2H),2.38-2.44(dd,1H),2.19-2.30(m,3H),2.08-2.13(m,1H),1.82-1.89(m,4H),1.08-1.65(m,8H),0.95 (s,3H).

[0029] 1.2, 17α-hydroxy-19-desmethylpregn-4-ene-3,20-dione (3)

[0030] Add methanol (480ml) and metal sodium (1.13g...

Embodiment 2

[0042] 2.1, 19-desmethyl-21-phenylsulfinylpregna-4,17(20),20-triene (2)

[0043] Add compound 1 (10g, 33.5mmol), dichloromethane (500ml), triethylamine (17g, 167.5mmol) into the reaction flask, cool to -5°C, dropwise add benzenesulfenyl chloride (9.68g, 67mmol) Dichloromethane solution (35ml), keep the reaction temperature at -5°C for 30 minutes, add 150ml of water and 30ml of methanol, stir for 10 minutes, separate layers, wash with saturated NaCl solution, dry, concentrate the solvent, recrystallize to obtain a white solid product, The dried weight is 12.3g, and the yield is 90% (the product purity is the same as in Example 1.1).

[0044] 2.2, 17α-hydroxy-19-desmethylpregna-4-ene-3,20-dione (3)

[0045] Add methanol (500ml) and metal sodium (1.13g, 47.2mmol) into the reaction flask, add compound 2 (24g, 59mmol) after the reaction, raise the temperature to 50°C for 2 hours, add trimethyl phosphite (8.12g, 64.9 mmol), reacted for 1 h, added HCl, poured into water, precipitat...

Embodiment 3

[0057] 3.1, 19-desmethyl-21-phenylsulfinylpregna-4,17(20),20-triene (2)

[0058] Add compound 1 (10g, 33.5mmol), dichloromethane (500ml), triethylamine (17g, 167.5mmol) into the reaction flask, cool in an ice bath at 0°C, dropwise add benzenesulfenyl chloride (9.68g, 67mmol) Dichloromethane solution (35ml), keep the reaction temperature at -0°C for 30 minutes, add 150ml of water and 30ml of methanol, stir for 10 minutes, separate layers, wash with saturated NaCl solution, dry, concentrate the solvent, and recrystallize to obtain a white solid product, The dried weight is 11g, and the yield is 80% (the product purity is the same as in Example 1.1).

[0059] 3.2, 17α-hydroxy-19-desmethylpregn-4-ene-3,20-dione (3)

[0060]Add methanol (500ml) and metal sodium (1.13g, 47.2mmol) to the reaction flask, add compound 2 (24g, 59mmol) after the reaction, raise the temperature to 65°C for 2 hours, add trimethyl phosphite (8.12g, 64.9 mmol), reacted for 1 hour, cooled, added HCl, poured...

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Abstract

The invention relates to the field of synthesis of compounds, in particular to a new method for synthesizing 6- methyl-17alpha-acetoxyl-19-norpregna-4,6-dialkyl-3,20-diketone. According to the method provided by the invention, norethindrone is taken as starting material to prepare 6- methyl-17alpha-acetoxyl-19-norpregna-4,6-dialkyl-3,20-diketone, the method provided by the invention has the advantages that the defects in the prior art are overcome, operation is simplified and production cost is reduced, related reactions and operations are simple, yield is high, and the yield of each step is 80% or above.

Description

technical field [0001] The invention relates to the field of compound synthesis, in particular to a new method for synthesizing 6-methyl-17α-acetoxy-19-norpregna-4,6-diene-3,20-dione. Background technique [0002] 6-Methyl-17α-acetoxy-19-norpregna-4,6-diene-3,20-dione: [0003] [0004] It is a new type of high-efficiency oral progestin, which has the characteristics of good contraceptive effect, small toxic and side effects, convenient use and safety. 6-Methyl-17α-acetoxy-19-norpregna-4,6-diene-3,20-dione was researched and developed by Theramex Company and was launched in France in 1985. In western countries, 6-methyl-17α-acetoxy-19-norpregna-4,6-diene-3,20-dione has been widely used as the fourth-generation contraceptive. In addition, 6-methyl-17α-acetoxy-19-norpregna-4,6-diene-3,20-dione has an effect on endometrial displacement (Chinese Pharrnacological Bulletin 2004 Nov; 20(11): 1215 -7), it has a good effect on reversing the multidrug resistance of breast cancer...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
Inventor 黄云生夏秋
Owner 黄云生
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