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Chenodeoxycholic acid synthesis method

A technology of chenodeoxycholic acid and its synthesis method, which is applied in the field of organic chemical synthesis, can solve the problems of high price, heavy pollution, and low yield, and achieve the effects of convenient industrial production, low cost, and increased yield

Inactive Publication Date: 2011-05-18
ZHENGZHOU UNIV
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Problems solved by technology

The traditional extraction process is complex in operation and low in yield, (Pharmaceutical Industry, 1987, 18 (9), 416; Chinese Journal of Biochemical Medicine, 1996, 17 (1), 17; Applied Technology, 1998, (4), 9; CN1850846A ) cannot meet the needs of modern industry
The chemical synthesis of chenodeoxycholic acid has also been reported (Japanese Journal of Chemistry 1955, 76 (3), 297; J Org Chem 1982, 47 (2): 2331; Journal of Biochemical Medicine 1987, 1, 6 ; Tap Chi Duoc Hoc2004, 44(1), 11; CN1869043A), but there are generally problems of low yield and high pollution, especially in the oxidation reaction, most of which are expensive and polluting large reagent

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  • Chenodeoxycholic acid synthesis method

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Embodiment Construction

[0027] For a better description of the present invention, examples are as follows:

[0028] (1) Preparation of methyl cholic acid: Take 5.1 g of cholic acid, add 15 ml of anhydrous methanol, and heat to dissolve it completely. Reflux for 3 hours, add 0.4ml of concentrated hydrochloric acid, stop the reaction after 30min, cool slowly, and filter to obtain 5.05g of methyl cholic acid, with a yield of 95%. 1 HNMR (CDCl 3 ): δ 0.70 (s, 3H, 18-CH 3 ), 0.90 (s, 3H, 19-CH 3 ), 0.98 (d, 3H, 21-CH 3 ), 3.50 (m, 1H, 3β-H), 3.67 ( s, 3H, OCH 3 ), 3.87 (s, 1H, 7β-H), 3.99 (s, 1H, 12β-H).

[0029] (2) Preparation of 3α,7α-diacetyl-12α-hydroxycholate methyl ester: Take 4.71g (11mmol) of methyl cholate and put it in a 100ml flask, add 30ml of dichloromethane and 3.8ml of triethylamine, and keep at room temperature Stir, add 2.7ml (28.6mmol) of acetic anhydride dropwise, and then add 20mg of N,N-lutidine catalyst, the reaction time is 7 hours, distill off dichloromethane, pour into wat...

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Abstract

The invention relates to a chenodeoxycholic acid (3 alpha, 7 alpha-dihydroxyl-5 belta-cholestane-24-acid) chemical synthesis method, belonging to the field of organic chemical synthesis. Chenodeoxycholic acid is prepared by the following steps of: (1) preparing cholate; (2) preparing 3 alpha, 7 alpha-acetyl-12 alpha-hydroxy cholate; (3) preparing 3 alpha, 7 alpha-acetyl-12-oxo-chenodeoxycholic acid ester; (4) preparing 12-oxo-chenodeoxycholic acid; and (5) preparing chenodeoxycholic acid. The application of the method for synthesizing chenodeoxycholic acid has the advantages of high yield rate, low cost and no pollution and is particularly convenient for industrial production.

Description

technical field [0001] The invention relates to a chemical synthesis method of chenodeoxycholic acid (3α, 7α-dihydroxy-5β-cholestane-24-acid), which belongs to the field of organic chemical synthesis. Background technique [0002] Chenodeoxycholic acid (3α,7α-dihydroxy-5β-cholestane-24-acid) Chenodeoxycholic Acid (CDCA for short), clinically used as a drug for dissolving cholesterol stones and correcting saturated bile, the main function is to reduce bile Large doses of CDCA can inhibit the synthesis of cholesterol and increase the secretion of bile in patients with cholelithiasis. Cholesterol is in an unsaturated state, thereby preventing the formation of cholesterol stones and promoting the dissolution and shedding of cholesterol in the stones. It also has significant anti-asthmatic, anti-inflammatory, antitussive and expectorant properties. [0003] Chenodeoxycholic acid is also the main intermediate for the synthesis of ursodeoxycholic acid (3α,7β-dihydroxy-5β-cholestan...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J9/00
Inventor 闫学斌张建业王庆录朱波刘宏民
Owner ZHENGZHOU UNIV
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