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Novel technology for oxosynthesis of pregnane 11-bit ketonic group

A compound, nitrogen oxide free radical technology, applied in the field of synthesis of pregnane 11-position ketone group, can solve problems such as multiple impurities and environmental protection problems

Inactive Publication Date: 2012-10-24
TIANJIN JINYAO GRP
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] Oxidation of 11α hydroxy to 11 ketone is currently frequently used CrO 3 11-keto is obtained, while Cr 6+ It has a strong oxidizing property, which will have a certain impact on the double bonds and hydroxyl groups on other positions of the steroid, and produce more impurities. At the same time, the substance and its reaction product Cr 2+ will cause certain environmental problems, so in recent years, researchers have been looking for more environmentally friendly and selective oxidants

Method used

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  • Novel technology for oxosynthesis of pregnane 11-bit ketonic group
  • Novel technology for oxosynthesis of pregnane 11-bit ketonic group
  • Novel technology for oxosynthesis of pregnane 11-bit ketonic group

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Experimental program
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Effect test

Embodiment 1

[0060]

[0061]Add 10mmol of compound 2.1 into 30ml of dichloromethane, add 12mmol of NaOCl in 20ml of aqueous solution while stirring, then add 0.15mmol of TEMPO, stir well at 20°C, react until there is no raw material after 4 hours, add saturated NaOCl 2 SO 3 The organic phase was washed several times with aqueous solution to remove TEMPO and inorganic salts. The organic layer was dried by adding anhydrous sodium sulfate, filtered, and then vacuum rotary evaporated to obtain the product after removing the organic solvent, yielding 9.0 mmol of 1.1 compound.

Embodiment 11

[0063] Add 10mmol of compound 2.1 into 30ml of dichloromethane, add 12mmol of NaOCl in 20ml of aqueous solution while stirring, then add 0.15mmol of TEMPO and 1mmol of NaBr, stir well at 20°C, react until there is no raw material after 1 hour, add saturated Na 2 SO 3 The organic phase was washed several times with aqueous solution to remove TEMPO and inorganic salts. The organic layer was dried by adding anhydrous sodium sulfate, filtered, and then vacuum rotary evaporated to obtain the product after removing the organic solvent, yielding 9.2 mmol of 1.1 compound.

Embodiment 12

[0065] Add 10mmol of compound 2.1 into 30ml of acetonitrile, add 12mmol of NaOCl in 20ml of aqueous solution while stirring, then add 0.15mmol of TEMPO and 1mmol of NaBr, stir fully at 20°C, react until there is almost no raw material after 2.5 hours, add saturated Na 2 SO 3 The organic phase was washed several times with aqueous solution to remove TEMPO and inorganic salts. The organic layer was dried by adding anhydrous sodium sulfate, filtered, and then vacuum rotary evaporated to obtain the product after removing the organic solvent, yielding 6.9 mmol of 1.1 compound.

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Abstract

The invention relates to a novel technology for oxosynthesis of pregnane 11-bit ketonic group, which is characterized in that a compound in a formula 2 uses piperidine nitroxide free-radical as an oxidation catalyst under the condition of an organic solvent, and uses positive valence halide as an oxidant to react to generate a compound in a formula 1.

Description

Technical field: [0001] The invention relates to a new process for synthesizing the 11-position keto group of pregnant. Background technique: [0002] The presence of oxygen-containing functional groups at C-11 in the steroidal structure is more important, and it is indispensable for anti-inflammatory effects and glucose metabolism. Xu Lu et al. reported (Applied Chemistry 1995, 1, 59) to analyze the conformation of steroidal anti-inflammatory drugs by means of molecular mechanics, and studied the correlation between the conformation and activity of such compounds. The results showed that not only in specific positions The substitution of the oxygen atom, and the steric position and steric energy of the oxygen atom are important factors affecting the activity of this type of compound. [0003] Some steroidal compounds with 11-hydroxyl, especially 11β-hydroxyl, have very important pharmacological activities. In addition, the introduction of 11-hydroxyl is also one of the imp...

Claims

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Application Information

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IPC IPC(8): C07J75/00C07J7/00C07J71/00C07J5/00
Inventor 卢彦昌孙亮韩英刘爱
Owner TIANJIN JINYAO GRP
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