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A technology of ursodeoxycholic acid and chenodeoxycholic acid, which is applied in the field of preparation of ursodeoxycholic acid, can solve the problems of low product yield and unprotected hydroxyl groups, and achieve high purity
Active Publication Date: 2011-03-23
ZHONGSHAN BAILING BIOTECHNOLOGY CO LTD
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[0010] There is a shortcoming in the second synthetic method reported in the current literature, that is, the oxidation reaction is carried out without protection of other hydroxyl groups other than the 7-position, so even under the action of a milder oxidant, a certain amount of By-products, although these by-products can be removed after refining, the final product yield is still low
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Embodiment 1
[0053] In a 2000 ml reaction flask, add 100 grams of chenodeoxycholic acid, 61 grams of maleic anhydride, 400 milliliters of acetone, 43.6 grams of diethylamine, and 2 grams of 2,6-lutidine. Raise the temperature to 38-40°C and maintain stirring at this temperature for 4-5 hours. After detecting the completeness of the reaction by TLC, 300 ml of water was added, and the acetone was removed by vacuum distillation to obtain a clear brown-yellow solution, which was cooled to 20-25°C. 10% hydrochloric acid was added dropwise to adjust the pH to 3.5-4.0, and turbidity appeared. After about 20 minutes, 300 ml of methanol was added, and crystallization occurred. Add 300 milliliters of water, and stir at 20-25 ° C for 2-3 hours, filter, wash with 200 milliliters of water, and dry to obtain 123.6 grams of white to off-white solid powder (formula III, 3a-ester-7a-hydroxy-5β-cholic acid , R-CDCA).
[0054] In a 2000 ml reaction flask, add 123.6 g of the product from the previous step,...
Embodiment 2
[0058] In a 2000ml reaction flask, add 100g of chenodeoxycholic acid, 59g of glutaric anhydride, 400ml of 3-methylfuran, 58.6g of tetramethylguanidine, heat up to 25-30°C, and Stirring was maintained for 7-9 hours. After detecting the completeness of the reaction by TLC, 300 ml of water was added, and the reactant was vacuum distilled to remove the organic solvent to obtain a brownish-yellow solution, which was cooled to 20-25°C. Add 10% hydrochloric acid dropwise to adjust the pH to 3.5-4.0. The temperature must be maintained below 30°C throughout the process, and turbidity occurs. After about 20 minutes, 220 ml of ethanol was added dropwise, and crystallization occurred. Continue to add 300 ml of water dropwise in 5-10 minutes, and stir at 20-25 ° C for 2-3 hours, filter, wash with 200 ml of water, and dry to obtain 127.4 grams of white to off-white solid powder (formula III, 3a-ester group-7a -hydroxy-5β-cholic acid, R-CDCA).
[0059] In a 2000 ml reaction flask, add 12...
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Abstract
The invention discloses a preparation method of ursodesoxycholic acid, which comprises the flowing steps of: a. carrying out 3-bit esterification on chenodeoxycholic acid to obtain 3-esterification protected chenodeoxycholic acid; b. carrying out 7-bit oxidation reaction on 3-bit ester to obtain 3-estergroup-7-oxocompounds; c. carrying out hydrolysis reaction or reduction reaction on the 3-estergroup-7-oxocompounds; d, carrying out 7-bit reduction reaction on 3a-hydroxy-7-oxo-5 beta-cholic acid or hydrolysis reaction on 3a-estergroup-7 beta- hydroxyl-5 beta-cholic acid to obtain crude products of the ursodesoxycholic acid; e. forming salt through the crude products of the ursodesoxycholic acid and organic base; and f. carrying out steps such as water adding dissolution, acid adding crystallization and the like on ursodesoxycholate to obtain pure ursodesoxycholic acid products with the purity higher than 99.0 percent. The invention aims at overcoming the defects in the prior art to provide a novel method for preparing the ursodesoxycholic acid, and the ursodesoxycholic acid prepared by the method has high yield and high purity.
Description
technical field [0001] The invention relates to a preparation method of ursodeoxycholic acid. Background technique [0002] Bear bile is a traditional precious medicinal material. As the main active ingredient contained in bear bile, ursodeoxycholic acid has a strong effect of promoting the hydrolysis of fat and fatty acid. It is mainly used clinically to treat various liver and gallbladder diseases and digestive tract diseases. Disease; the chemical name of ursodeoxycholic acid is 3α, 7β-dihydroxy-5β-cholic acid, its English name is Ursodeoxycholic acid, and its structural formula is: [0003] [0004] At present, there are many synthetic routes and preparation methods of ursodeoxycholic acid in various patents and literatures, and the preparation methods of ursodeoxycholic acid generally have the following types: [0005] 1. Extract and separate bear bile from live bears; [0006] 2. A synthetic method using animal cholic acids (including: cholic acid, chenodeoxycholi...
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