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Method for synthesizing lithocholic acid from cholic acid

A synthesis method and lithocholic acid technology, which are applied in the directions of steroids, organic chemistry, etc., can solve the problems of unsuitability for industrial production and high cost, and achieve the effects of less side reactions, simple post-processing, and short synthetic route.

Active Publication Date: 2017-08-04
JIANGSU JIAERKE PHARMA GRP CORP
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  • Abstract
  • Description
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Problems solved by technology

[0006] In this synthetic route, the total yield is only 23%, and expensive platinum dioxide catalyst is used, the cost is high, and it is not suitable for industrial production

Method used

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  • Method for synthesizing lithocholic acid from cholic acid
  • Method for synthesizing lithocholic acid from cholic acid
  • Method for synthesizing lithocholic acid from cholic acid

Examples

Experimental program
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Embodiment 1

[0048] 1, the synthesis of formula (2 ') compound

[0049]

[0050]Dissolve cholic acid (10g, 24.5mol) in pyridine (50mL), add succinic anhydride (3.43g, 34.3mmol), heat up to 80°C for 17 hours, add 300mg of succinic anhydride, react for 7 hours, add 300mg Succinic anhydride was reacted for another 7 hours, and 200 mg of succinic anhydride was added to react for 12 hours. After the reaction of the raw materials was detected by TLC, the reaction liquid was cooled to room temperature, poured into dilute HCl aqueous solution (55 mL of concentrated hydrochloric acid + 500 mL of water), added 100 mL of ethyl acetate and stirred at room temperature for 20 minutes. The layers were separated, and the aqueous phase was extracted with ethyl acetate (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 dry in vacuo to obtain the crude compound of formula (2') (white solid, 12....

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Abstract

The invention discloses a method for synthesizing lithocholic acid from cholic acid. According to the method, cholic acid is used as a starting raw material, and lithocholic acid is synthesized through the following four steps of reaction: selective protection of 3alpha-OH; oxidation of 7alpha-OH and 12alpha-OH into carbonyl groups; hydrolysis; and Huang Min-lon reduction. The raw material used in the method is easily available and cheap, and the method is few in synthesis steps and side reactions, simple in after-treatment, high in overall yield and suitable for 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 cholic acid as a raw material. Background technique [0002] Lithocholic acid, also known as 3α-hydroxy-5β-cholanic acid, is a bile acid, and its structure is shown in formula (i). Studies have shown that lithocholic acid and its derivatives have various physiological activities, such as antibacterial, antifungal activity (Farmaco Sci.39 (4) (1984) 305-315), antitumor activity (Proc.Natl.Acad.Sci.US A.109(42)(2012)16906-16910), α-2,3-sialyltransferase inhibitory activity (Chem.Commun.(6)(2006)629-631), protein tyrosine phosphatase 1B Inhibitory activity (Bioorg.Med.Chem.Lett.22(23)(2012)7237-7242), TGR5 receptor activator (J.Med.Chem.51(6)(2008)1831-1841), etc. [0003] [0004] There are few reports on the synthesis of lithocholic acid. In 1946, it was reported that deoxycholic acid was used as the starting ma...

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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