Method for preparing 16-dehydrogenated pregnane dehydropregnenolone acetate compound by using photosensitized oxidation of blue LED (light-emitting diode) light source

A diketene alcohol acetic acid, photosensitive oxidation technology, applied in the direction of steroids, organic chemistry, etc., can solve the problems of water resource waste cost, energy waste, cost occupied by filter systems, etc., to save electric energy and eliminate environmental pollution problems Effect

Inactive Publication Date: 2014-05-07
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

Since the maximum absorption wavelength of the photosensitizer hematoporphyrin is around 400nm, the reactor needs to use doped quartz glass equipment to filter out the light band below 380nm, which means that only a small part of the light energy output by the mercury lamp is effectively used. As a result, a lot of energy wasted; at the same time, the design and manufacture of the filter system also accounted for a large proportion of the cost
In addition, the radiant heat generated by the 10kW mercury lamp requires a large amount of cooling water to cool down, which is also an important reason for the waste of water resources and the rising cost

Method used

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  • Method for preparing 16-dehydrogenated pregnane dehydropregnenolone acetate compound by using photosensitized oxidation of blue LED (light-emitting diode) light source
  • Method for preparing 16-dehydrogenated pregnane dehydropregnenolone acetate compound by using photosensitized oxidation of blue LED (light-emitting diode) light source
  • Method for preparing 16-dehydrogenated pregnane dehydropregnenolone acetate compound by using photosensitized oxidation of blue LED (light-emitting diode) light source

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0034] The used internal immersion bubbling photochemical reactor is composed of a container with an air inlet at the bottom, a sink and a 10W blue LED lamp with an emission wavelength greater than 380nm.

[0035] Such as figure 1 As shown, the sinker made of glass capable of filtering light below 380nm is a U-shaped interlayer container with a cooling water inlet and outlet, and the sinker is installed in the container; the blue A colored LED light is placed in the inner cavity of the sink.

[0036] Utilize the above-mentioned internal immersion bubbling photochemical reactor to oxidatively degrade pseudodiosgenin diacetate into 3β-hydroxy-pregna-5(6),16(17)-dien-20-one acetate:

[0037] At room temperature (such as 25°C), in a 500mL round-bottomed flask, dissolve 10g of pseudodiosgenin diacetate, 37mg of hematoporphyrin, 5.5mL of triethylamine and 3.7mL of acetate in 330mL of In 2-methyltetrahydrofuran, stir and mix evenly to prepare a photochemical reaction solution. Tra...

Embodiment 2

[0045] Utilize the internal immersion bubbling photochemical reactor of Example 1, oxidative degradation pseudodiosgenin diacetate is 3β-hydroxyl-pregna-5(6),16(17)-dien-20-one acetate:

[0046] At room temperature (such as 25°C), in a 500mL round-bottomed flask, dissolve 10g of pseudodiosgenin diacetate, 37mg of hematoporphyrin, 5.5mL of triethylamine and 3.7mL of acetate in 330mL of ethyl acetate, stir and mix evenly, and prepare photochemical reaction solution. Transfer the photochemical reaction liquid to the container of the inner immersion bubbling photochemical reactor, and pass oxygen into the photochemical reaction liquid from the bottom of the container for bubbling, adjust the flow of oxygen to make the bubbles uniform; open the inner immersion bubbling photochemical reactor The cooling water valve of the reactor is opened, and the blue LED light of 10W installed in the sinking trap in the bubbling photoreactor is turned on, and the photosensitive oxidation reactio...

Embodiment 3

[0052] Using the internal immersion bubbling photochemical reactor of Example 1, the method for oxidatively degrading pseudosagagenin diacetate into 5α-pregnene-12,20-diketone-3β-hydroxyacetate is basically the same as that of Example 1. Same, just change 2-methyltetrahydrofuran into dioxane, the raw material pseudodiosgenin diacetate is changed into pseudosacegenin diacetate, and utilize high pressure liquid chromatography (HPLC) to monitor the reaction process (HPLC detection condition Same as Example 1). At the end of the photosensitive oxidation reaction, the conversion rate of the raw material pseudosacetin diacetate was 98.8%.

[0053] The obtained light brown crystalline 5α-pregnene-12,20-diketone-3β-hydroxyacetate was 6.4 g (purity: 96.8%), and the yield was 74.4%.

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Abstract

The invention belongs to the field of organic photochemical synthesis, and particularly relates to a method for preparing a 16-dehydrogenated pregnane dehydropregnenolone acetate compound by using the photosensitized oxidation of a blue LED (light-emitting diode) light source. According to the invention, in the presence of a photosensitizer hematoporphyrin, a catalyst triethylamine and acetate, by taking a blue LED lamp as a light source, false steroid sapogenin di-acetate is subjected to photosensitized oxidation reaction, and then the obtained product is subjected to acid elimination reaction so as to obtain the 16-dehydrogenated pregnane dehydropregnenolone acetate compound. According to the invention, the conversion rate of false steroid sapogenin di-acetate is over 98%, and the yield of the 16-dehydrogenated pregnane dehydropregnenolone acetate compound is up to 82.6%. According to the invention, by replacing a light source high-voltaqe mercury lamp in photosensitized oxidation with the blue LED lamp, on the premise of comparative target product yield, an effect of saving over 40 times of electric energy and a lot of water resources is achieved by using the blue LED lamp. The method disclosed by the invention provides a new technique for green chemistry in the industrial production of steroidal drugs.

Description

technical field [0001] The invention belongs to the field of organic photochemical synthesis, and in particular relates to a method for preparing 16-dehydropregnadienone alcohol acetate compounds by photosensitive oxidation using a blue LED light source. Background technique [0002] There are more than 300 kinds of steroid drugs, which are widely used in the fields of anti-inflammatory, anti-allergic, endocrine regulation, anti-aging and contraception. This type of drugs is the second largest drug family after antibiotics. 16-Dehydropregnenolone acetate (16-DPA) is the most important intermediate of steroid drugs, and more than 70% of steroid drugs are produced from it. 16-DPA is prepared from diosgenin through three steps of thermal cracking, oxidation and elimination. At present, the oxidation reaction of pseudodiosgenin uses chromic anhydride oxidation technology at home and abroad, but chromic anhydride is a highly toxic and highly corrosive oxidant, and the discharge ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00
Inventor 李超王雪松程学新张宝文
Owner TECHNICAL INST OF PHYSICS & CHEMISTRY - CHINESE ACAD OF SCI
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