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Method for synthesizing lithocholic acid from hyodesoxycholic acid

A technique for synthesizing hyodeoxycholic acid and its synthesis method, which is applied in the field of synthesizing lithocholic acid, can solve the problems of high reaction risk factor, unfavorable industrialization, long synthesis route, etc., and achieve less side reactions, high total yield, and simple post-treatment Effect

Active Publication Date: 2017-07-25
JIANGSU JIAERKE PHARMA GRP CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0010] Metal sodium is used in this synthetic route, and the reaction risk factor is relatively large, which is not conducive to industrialization
And the synthetic route is long, and the total yield is low

Method used

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  • Method for synthesizing lithocholic acid from hyodesoxycholic acid
  • Method for synthesizing lithocholic acid from hyodesoxycholic acid
  • Method for synthesizing lithocholic acid from hyodesoxycholic acid

Examples

Experimental program
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Effect test

Embodiment 1

[0037] 1, the synthesis of formula (2) compound

[0038]

[0039] Hyodeoxycholic acid (5 g, 12.7 mol) was dissolved in a mixed solvent of acetone (50 mL) and water (25 mL), NBS (3.95 g, 22.2 mmol) was added, and reacted at room temperature for 2 hours in the dark. After TLC detects that the reaction of raw materials is complete, add 30 mL of saturated NaHSO 3 The solution quenched the reaction. Add 200 mL of water and 30 mL of dichloromethane, and stir at room temperature for 10 minutes. The layers were separated, and the aqueous phase was extracted with dichloromethane (40 mL×4). The organic phases were combined, washed successively with saturated brine (30mL×1), anhydrous Na 2 SO 4 dry. Concentrate under reduced pressure and purify by silica gel column chromatography (DCM:MeOH=40:1) to obtain the compound of formula (2) (white solid, 4.5 g), with a mass yield of 90%. 1 H NMR (400MHz, DMSO-d 6 )δ 3.42–3.33 (m, 1H), 0.89 (d, J=6.4Hz, 3H), 0.74 (s, 3H), 0.61 (s, 3H). ...

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Abstract

The invention discloses a method for synthesizing lithocholic acid, comprising: using hyodesoxycholic acid as a start material, and performing two-step reaction of 6Alpha-OH selective oxidation and Huang Minglon reduction to synthesize the lithocholic acid. The start material herein is low in price and easy to obtain, the synthetic steps are short, posttreatment is simple, few side reactions are employed, and the method is applicable to industrial production.

Description

technical field [0001] The invention belongs to the field of organic chemistry, and in particular relates to a method for synthesizing lithocholic acid by using hyodeoxycholic acid as a raw material. Background technique [0002] Lithocholic acid, also known as 3α-hydroxy-5β-cholanic acid, has a structure as shown in formula (i). Studies have shown that lithocholic acid and its derivatives have various physiological activities, such as antitumor activity (Bioorg.Med.Chem.Lett.6 (6) 1996,637-642); Normal cells have little toxicity (Oncotarget 2(10)(2011) 761-782); have antibacterial and antifungal activities (Farmaco Sci.39(4)(1984) 305-315). [0003] At present, lithocholic acid is mainly extracted from animal bile, the content is low, and the source is limited, which cannot meet the market demand; therefore, the development of novel and efficient synthetic routes of lithocholic acid has potential application value. [0004] [0005] There are few reports on the synthes...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 顾向忠蒋澄宇仇文卫高伟
Owner JIANGSU JIAERKE PHARMA GRP CORP
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