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Method for synthesizing 16-dehydropregndiketonic alcohol acetic ester and its analogs

A technology of diketene alcohol acetate and the like, which is applied in the field of chemical synthesis of drugs, can solve the problems of expensive metal catalysts, environmental pollution and high risk, achieves less stringent temperature control requirements, is environmentally friendly, and improves product yield. rate effect

Inactive Publication Date: 2009-03-18
TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Most of these degradation methods use CrO 3 As an oxidant, this toxic metal oxidant can cause environmental pollution
instead of CrO 3 In the method of making oxidizing agent, also unavoidably used such as potassium permanganate oxidizing agent, the metal catalyst containing tungsten or vanadium, or hydrogen peroxide (H 2 o 2 ) etc., there are also some problems in this type of method, such as fundamentally failing to eliminate environmental pollution, metal catalysts are more expensive, high risk, etc.

Method used

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  • Method for synthesizing 16-dehydropregndiketonic alcohol acetic ester and its analogs
  • Method for synthesizing 16-dehydropregndiketonic alcohol acetic ester and its analogs
  • Method for synthesizing 16-dehydropregndiketonic alcohol acetic ester and its analogs

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Oxidative degradation of semagenin to 5α-pregnene-12,20-diketone-3β-hydroxyacetate:

[0029] Dissolve 10 g (0.02 mol) of safranin acetate in 75 ml of acetic anhydride, add 2.6 g (0.022 mol) of pyridine hydrochloride, heat to reflux, and after the conversion of raw materials is complete (about 4 hours), distill under reduced pressure Go out most of acetic anhydride, under stirring, remaining mixture is poured into 100ml ice water, produces a large amount of yellow precipitates, and the precipitate filtered out is recrystallized with methanol, and the product obtained is pseudosacetin, and the productive rate is 70% (documentation value was 84%).

[0030] The light source used in the photooxidation reaction experiment is a medium-pressure mercury lamp, which is built in a cold jacket made of quartz, and a Pyrex glass photoreactor with a ventilation device is used. Take 2g (0.004mol) of pseudosemagenin in the light reaction vessel, and add the concentration of 1 × 10 -3 ...

Embodiment 2

[0032] Oxidative degradation of semagenin to 5α-pregnene-12,20-diketone-3β-hydroxyacetate:

[0033] The light source used in the photooxidation reaction experiment is a medium-pressure mercury lamp, which is built in a cold jacket made of quartz, and a Pyrex glass photoreactor with a ventilation device is used. Get 2g (0.004mol) pseudosemagenin synthesized in embodiment 1 in the photoreaction container, adding concentration is 2 * 10 -3 mol / L acetonitrile solution of hematoporphyrin in 20ml, then add 1ml (about 0.012mol) of pyridine and 1ml (about 0.01mol) of acetic anhydride, and pass through oxygen. The optical filter passes light with a wavelength of 380 to 600 nm. Use HPLC to track the reaction, stop the light immediately when the pseudosacenagenin is completely converted, evaporate the acetonitrile solvent under reduced pressure, then add 15ml of glacial acetic acid, heat and reflux for 3 hours, concentrate, dissolve in petroleum ether, wash with dilute alkaline water un...

Embodiment 3

[0035] Oxidative degradation of diosgenin to 16-dehydropregnadienol acetate:

[0036] Take 20g (48.3mmol) of diosgenin in a 500ml three-necked bottle, add about 150ml of acetic anhydride, stir and reflux with nitrogen for one hour, stop heating, and distill out about 30ml of acetic anhydride solvent under reduced pressure after cooling down slightly. Add 6.5g (56.3mmol) of pyridine hydrochloride into the three-necked flask, and reflux at about 160°C for 5 hours to obtain a dark red solution. Distill under reduced pressure to remaining 30ml reaction mixture, this mixture is poured into 100ml ice water under agitation, produces a large amount of yellow precipitates, and the precipitate filtered out is recrystallized with methanol, and the resulting product is pseudodiosgenin, and vacuum drying gives 18g light yellow solid, The yield was 75%.

[0037] The light source used in the photooxidation reaction experiment is a medium-pressure mercury lamp, which is built in a cold jacke...

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Abstract

The invention belongs to medicine chemical synthesis field, especially relates to method for synthesizing 16- dehydrogenating pregnene acyloin acetic ester and medicine intermediate of the same kind with steroid saponin. The pseudosapogenin cracked from steroid saponin reacts with oxygen under existence of light and sensitizer, or with catalyst pyridine and acetic anhydride, and product is acidolysized directly to get final product. The invention is characterized by elimination of chromic anhydride pollution used as oxidant, irrigid temperature control, simple post treatment process, and increased productivity.

Description

technical field [0001] The invention belongs to the field of chemically synthesized drugs, and is particularly suitable for the synthesis method of preparing 16-dehydropregnenone alcohol acetate or similar drug intermediates from steroid sapogenins. Background technique [0002] 16-Dehydropregnane dienone acetate (3β-hydroxy-pregna-5(6), 16(17)-dien-20-one acetate), known as "diene" in the industrial sector. Its congeners are: 3β-hydroxy-5α-pregnant-16(17)ene-12,20-dione acetate, 3β-hydroxy-5α-pregnant-16(17)enene-20-one acetate, 3β-hydroxy-5β-pregna-16(17)en-20-one acetate, 3β,12β-dihydroxy-5α-pregna-16(17)en-20-one acetate, etc. [0003] 16—Dehydropregnone dienone acetate, 3β-hydroxy-5α-pregna-16(17)en-20-one acetate and 3β-hydroxy-5α-pregna-16(17)en-12 , 20-diketone acetate is an important intermediate of steroid hormone drugs. The production capacity of 16-dehydropregnone dienone alcohol acetate in my country is more than 1,000 tons, and it is an important intermediat...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07J7/00
Inventor 程学新张焱刘颙颙王雪松张宝文
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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