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Synthesis process of a pregnane compound

A synthesis method and compound technology, applied in the field of synthesis of Δ9, pregnane steroid compounds, can solve the problems of high yield, high cost, and increased cost, and achieve the effects of high yield, low cost, and easy operation

Active Publication Date: 2007-04-25
ZHEJIANG XIANJU XIANLE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0008] This invention improves the previous method, directly eliminates the C11-hydroxyl group with phosphorus pentachloride (or phosphorus trichloride, phosphorus oxychloride, etc.), Δ 9，11 The selectivity of conversion is greatly improved, Δ 11，12 -The content of pregnane by-products can be reduced to 2%, but because the elimination reagent also affects the C21-hydroxyl in the starting material, in order to protect the C21-hydroxyl, the more toxic and expensive ethyl chloroformate is used , which increases the cost
[0009] Summarizing the above two C11-hydroxyl elimination methods, the first method is simple, but the quality is poor and the yield is low; the product obtained by the second method has high purity and high yield, but the cost is also high

Method used

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  • Synthesis process of a pregnane compound
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  • Synthesis process of a pregnane compound

Examples

Experimental program
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Effect test

Embodiment 1

[0023] Implementation Example 1. Put 40g of 11α-hydroxyl-pregna-1,4,16-triene-3,20-dione into a three-neck flask equipped with a stirrer and a low-temperature thermometer, add 400ml tetrahydrofuran, and place in a freezer Lower the temperature to below -50°C, slowly add 40g of phosphorus pentachloride in portions, then keep the temperature at -50°C for 2 hours, then raise the temperature to 0°C, continue the reaction for 30 minutes, and dissolve the water into 1000ml of ice water, add 25% hydroxide Sodium adjusted PH = 7, stirred for 2 hours, filtered, dried, and the obtained Δ 9，11 - Pregnant compound HPLC purity 95.6%, Δ 11，12 -Isomer impurity 2.0%, yield 94.5%.

Embodiment 2

[0024] Implementation Example 2. Put 40g of 11α-hydroxyl-pregna-1,4-diene-3,20-dione into a three-neck flask equipped with a stirrer and a low-temperature thermometer, add 400ml tetrahydrofuran, and place in a freezer to cool down to Below -50°C, slowly add 40g of phosphorus pentachloride in portions, then keep the temperature at -50°C for 2 hours, then raise the temperature to 0°C, continue the reaction for 30 minutes, and water it into 1000ml of ice water, add 25% sodium hydroxide to adjust PH=7, stirred for 2 hours, filtered and dried, the obtained Δ 9，11 - Pregnant compound HPLC purity 93.6%, Δ 11，12 -Isomer impurity 2.2%, yield 94.5%.

Embodiment 3

[0025] Implementation Example 3. Put 16α-methyl-11α into a three-necked flask equipped with a stirrer and a low-temperature thermometer, 17α-dihydroxy-pregna-4-ene-3,20-dione 40g, add 400ml acetonitrile, place Cool down to -30°C in the freezer, slowly add 40ml of phosphorus trichloride dropwise, and finish adding in 1 hour, then raise the temperature to -20°C and keep it warm for 2 hours, TLC until the raw material point is less than 1%, water analysis to 1000ml of ice water, add Adjust PH=7 with 25% sodium hydroxide, stir for 2 hours, filter, and dry to obtain Δ 9，11 - Pregnant compound HPLC purity 92.3%, Δ 11，12 -Isomer impurity 3.2%, yield 90%.

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Abstract

The invention discloses a synthesizing method of Delt9,11-pregnene compound, which is characterized by the following: adopting 21-non-hydroxylating pregnene compound as starting material; reacting with phosphorus pentachloride, phsophorus trichloride or phosphorus oxytrichloride in the organic solvent of tetrahydrofuran and acetonitrile; eliminating C11-hydroxy; obtaining the product with purity over 95% and the content of impurity isomer between 2 and 4%.

Description

Technical field: [0001] The present invention relates to a kind of synthetic method of pregnant steroid compound, especially Δ 9，11 - A synthetic method for a pregnant compound, belonging to the technical field of medicinal chemistry. Background technique: [0002] Δ 9，11 -pregnoid compound is a common intermediate in the synthetic process of steroidal corticosteroids. The classic synthetic method is the upper desulfurization method. See Peng Sixun's "Pharmaceutical Chemistry", Chemical Industry Press, 1986, P400-447, and its reaction process is as follows: [0003] [0004] Δ 9 11 -pregna Δ 11 12 -by-product [0005] In this reaction, p-toluenesulfonyl chloride and C11-hydroxypregnant compound are esterified in pyridine solution to form sulfonate, and then acetic acid and sodium acetate are used to eliminate C11-sulfonate to form Δ 9，11 -Pregnant intermediates with 10-15% Δ 11，12 - Pregnant by-product formation, reducing quality and yield. [0006] Patent applicat...

Claims

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Application Information

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IPC IPC(8): C07J7/00C07J75/00
Inventor 洪用剑朱秀兰
Owner ZHEJIANG XIANJU XIANLE PHARMA
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