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Synthesis method of 3beta, 7beta (alpha) dihydroxy-5beta-cholanic acid

A technology of cholic acid and dihydroxy, which is applied in the field of organic chemical synthesis, can solve the problems of high price and achieve the effect of low price, less impurities and simple process route

Pending Publication Date: 2022-03-01
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0005] At present, there is no report on the method of synthesizing these two substances at home and abroad, resulting in very expensive prices for the reference substances of these two substances on the market

Method used

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  • Synthesis method of 3beta, 7beta (alpha) dihydroxy-5beta-cholanic acid
  • Synthesis method of 3beta, 7beta (alpha) dihydroxy-5beta-cholanic acid
  • Synthesis method of 3beta, 7beta (alpha) dihydroxy-5beta-cholanic acid

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preparation example Construction

[0066] Such as figure 1 Shown, a kind of 3β, the synthetic method of 7β dihydroxy-5β-cholanic acid and 3β, 7α dihydroxy-5β-cholic acid, the starting material used is chenodeoxycholic acid, and concrete steps are as follows:

[0067] a, preparation of compound B (7-ketolithocholic acid)

[0068] Dissolving compound A (chenodeoxycholic acid) in acetone, lowering the temperature, adding an oxidizing agent to carry out oxidation reaction, after the reaction is complete, adding a reducing agent to terminate the reaction. Acetone was distilled off, filtered and washed to obtain the wet crude compound B. Compound B was suspended in 2 times the volume of methanol, heated to reflux for 2 hours, cooled to room temperature, filtered, washed and dried to obtain refined compound B.

[0069] b, preparation of compound C (7-ketolithocholate)

[0070] Compound B was dissolved in alcohol, catalyst was added, refluxed for 2 h, after the reaction was completed, sodium bicarbonate solution was...

Embodiment 1

[0078] Such as figure 2 As shown, the preparation method of 3β, 7β-dihydroxy-5β-cholanic acid in this embodiment comprises the following steps:

[0079] a, preparation of 7-ketolithocholic acid

[0080] In a 500mL reaction flask, add 50g of chenodeoxycholic acid (CDCA), 250mL of acetone, stir to lower the temperature below 0°C, slowly add 22.3g of bromine, continue to react for 3 hours after the addition of bromine, and take samples to measure the residual amount of CDCA as 2.379%, add 1.3g sodium bisulfite to terminate the reaction. Acetone was distilled off in vacuo, 100 mL of water was added, stirred for 30 min, filtered and washed to obtain 84.7 g of wet crude product of 7-ketolithocholic acid. Pour all the wet crude 7-ketolithocholic acid into a reaction flask, add 170mL of methanol, raise the temperature and reflux for 2h, cool down to room temperature, filter, wash and dry to obtain 40.8g of 7-ketolithocholic acid with an HPLC purity of 99.347%.

[0081] b, preparat...

Embodiment 2

[0090] Such as image 3 As shown, the preparation method of 3β, 7α dihydroxy-5β-cholanic acid in this embodiment comprises the following steps:

[0091] a. Preparation of 7-ketolithocholic acid

[0092] In a 500mL reaction flask, add 50g of chenodeoxycholic acid (CDCA), 350mL of acetone, stir to lower the temperature below 0°C, add 0.5mL of concentrated sulfuric acid, slowly add 125g of 10% sodium hypochlorite solution, and continue the reaction for 0.5 h, the residual amount of CDCA was measured to be 3.446% by sampling, and 1 g of hydrosulfite was added to terminate the reaction. Acetone was distilled off in vacuo, 100 mL of water was added, stirred for 30 min, filtered and washed to obtain 82.3 g of wet crude product of 7-ketolithocholic acid. Pour the wet crude product of 7-ketolithocholic acid into a reaction flask, add 165mL of methanol, raise the temperature and reflux for 2h, cool down to normal temperature, filter, wash and dry to obtain 40.3g of 7-ketolithocholic a...

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Abstract

The invention discloses a synthesis method of 3 beta, 7 beta dyhydroxyl-5 beta-cholanic acid and 3 beta, 7 alpha dyhydroxyl-5 beta-cholanic acid. According to the method, chenodeoxycholic acid is taken as an initial raw material, and a target product 3 beta, 7 beta-dihydroxyl-5 beta-cholanic acid (impurity H) or 3 beta, 7 alpha-dihydroxyl-5 beta-cholanic acid (impurity K) is obtained through 7-site hydroxyl oxidation, carboxyl protection, 3-site hydroxyl Mitsunobu reaction structure inversion, hydrolysis deprotection and 7-site keto reduction. The impurity H and the impurity K are prepared through the synthetic route, and the raw materials are wide in source and sufficient in supply; the method has the advantages of high yield, few side reactions and simple post-treatment, is suitable for large-scale preparation, and can provide standard substances and data support for subsequent related researches.

Description

technical field [0001] The invention belongs to the field of organic chemical synthesis, and specifically relates to a synthesis method of 3β, 7β dihydroxy-5β-cholanic acid and 3β, 7α dihydroxy-5β-cholanic acid. Background technique [0002] Ursodeoxycholic acid UDCA is a non-toxic hydrophilic cholic acid, which can competitively inhibit the absorption of toxic endogenous cholic acid in the ileum, by activating the signaling network composed of calcium ions and protein kinase C, and by activating the cleavage activity Protein-based enzymes to increase the cholestatic effect. Ursodeoxycholic acid can also competitively replace toxic cholic acid molecules on cell-running organelles, preventing hepatocytes and cholangiocytes from being damaged by more toxic cholic acids. Clinically, ursodeoxycholic acid is mainly used to dissolve cholesterol gallstones, primary biliary cirrhosis PBC, chronic hepatitis C, and also used for alcoholic liver disease, non-alcoholic fatty liver, ben...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C12P33/06C07J9/00
CPCC12P33/06C07J9/005
Inventor 秦和平张和平刘涛祝国祥秦帅帅林志锋凌芬娜
Owner ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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