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Chenodeoxycholic acid and preparation method thereof

A technology of chenodeoxycholic acid and cholic acid, which is applied in the field of drug synthesis, can solve the problems of large environmental impact, and achieve the effects of mild conditions, high yield and strong reproducibility

Active Publication Date: 2019-05-17
SOUTH CHINA UNIV OF TECH +1
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The current yield of the synthesis route using hyodeoxycholic acid as raw material is 26%, but this route uses chlorobenzoquinone, which has a greater impact on the environment

Method used

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  • Chenodeoxycholic acid and preparation method thereof
  • Chenodeoxycholic acid and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0015] A kind of preparation method of chenodeoxycholic acid, see figure 1 , including the following steps:

[0016] Carry out the chemical reaction according to the following formula:

[0017]

[0018] In the embodiment of the present invention, 3α, 7α-dihydroxy-5α-cholanic acid (abbreviation: allochodeoxycholic acid) (A) is used as raw material to obtain 3α, 7α-dihydroxy-5α-cholanic acid ester ( B), 3α,7α-dihydroxy-5α-cholanate (B) 3-position selective oxidation to 3-keto-7α-hydroxy-5α-cholanate (C), 3-keto-7α-hydroxy -Protection of the 7-position of 5α-acyloxy-5α-cholanate (C) gives 3-keto-7α-acyloxy-5α-cholanate (D), 3-keto-7α-acyloxy-5α-cholanic acid Ester (D) undergoes an oxidation reaction to obtain △1,4-3-keto-7α-acyloxy-unsaturated cholanoic acid ester (E), △1,4-3-keto-7α-acyloxy-unsaturated Cholanate (E) is subjected to catalytic hydrogenation to reduce the double bond to obtain 3-keto-7α-acyloxy-5β-cholanate (F), 3-keto-7α-acyloxy-5β-cholanate The 3-position ...

Embodiment 1

[0063] This embodiment provides a method for preparing chenodeoxycholic acid, comprising the following steps:

[0064] S1, preparation of intermediate B;

[0065] Add allchenodeoxycholic acid (1.0 g, 2.6 mmol), 15 mL of anhydrous methanol, and 100 μL of concentrated sulfuric acid into a reaction vessel equipped with a dry reflux condenser. After the addition, the reaction temperature is raised to 67° C., and the reaction is stirred for 4 h. After the reaction was completed, the solvent methanol was removed by rotary evaporation, and 20 mL of ethyl acetate was added to dissolve the residue, followed by 10 mL of saturated NaHCO 3 solution and water wash. The organic phase was washed with anhydrous MgSO 4 Dry to remove water, filter to remove anhydrous MgSO 4 , collected the organic phase, and distilled off the solvent under reduced pressure to obtain 1.0 g of white solid, which was intermediate B, yield: 99%.

[0066] The structural characterization data of intermediate B ar...

Embodiment 2- Embodiment 10

[0108] The preparation method of chenodeoxycholic acid provided in Example 2-Example 10 is basically similar to the operation of the preparation method of chenodeoxycholic acid provided in Example 1, except that the raw materials used and the specific conditions of each step are different.

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Abstract

The invention relates to the field of medicine synthesis, and in particular to chenodeoxycholic acid and a preparation method thereof. The preparation method of the chenodeoxycholic acid provided by the invention comprises the following steps of: using 3 alpha,7 alpha-dihydroxy-5 alpha-ursodeoxycholic acid as raw materials to form an intermediate compound E through chemical reaction; then, performing chemical reaction on the intermediate compound E to form the chenodeoxycholic acid. The structure formula of the intermediate compound E is shown in the description, wherein R1 is alkyl, alkenylor aromatic group; R2 is acyl. The preparation method has the advantages that extracted byproducts can be used as raw materials for fast synthesizing the chenodeoxycholic acid; each step in the process is mild in condition; the yield is high; the method is suitable for mass preparation.

Description

technical field [0001] The invention relates to the field of drug synthesis, in particular to a chenodeoxycholic acid and a preparation method thereof. Background technique [0002] Bile acids are important endogenous molecules associated with myriad biological functions, including cholesterol absorption and excretion, and play an important role in fat metabolism. Chenodeoxycholic acid is a natural primary bile acid, which widely exists in the bile of humans, livestock, and poultry, and is the main component of poultry bile such as chickens, ducks, and geese. Since Thistle and Schoenfirld discovered that chenodeoxycholic acid can treat gallstones, the clinical application of chenodeoxycholic acid has been continuously discovered. Since the 1970s, chenodeoxycholic acid has been mainly used in the treatment of gallstone disease and other hepatobiliary diseases. Later, it was found that chenodeoxycholic acid can not only treat various hepatobiliary diseases, but also has antib...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/00
Inventor 张雷黄欢李杉张和平
Owner SOUTH CHINA UNIV OF TECH
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