Method for synthesizing ursodeoxycholic acid using BA as raw material
AssigneeJiangsu Jiaerke Pharmaceuticals Group Corp., Ltd.
InventorsWenwei Qiu, Jie Wang
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Abstract
The present invention discloses a synthesis method of ursodeoxycholic acid by using the plant-derived compound BA as a raw material to synthesize ursodeoxycholic acid through the steps of ethylene glycol or neopentyl glycol protection, oxidation, Wittig reaction, deprotection, reduction and hydrolysis, etc. The raw materials used for the synthesis of ursodeoxycholic acid in the present invention are cheap and easy to get, the synthesis steps are easy to operate, the yield is high, the reaction is environmentally friendly, and the industrial production is convenient.
Claims17
A method for the synthesis of ursodeoxycholic acid by using BA as a raw material, wherein, the said method comprises the following steps:
- (a) in the first solvent, BA shown in formula (1) is protected by ethylene glycol to obtain the compound of formula (2);
- (b) in the second solvent, the compound of formula (2) is oxidized to obtain the compound of formula (3);
- (c) in the third solvent, the compound of formula (3) undergoes Wittig reaction to obtain the compound of formula (6);
- (d) in the fourth solvent, the compound of formula (6) is oxidized to obtain the compound of formula (7);
- (e) in the fifth solvent, the compound of formula (7) undergoes hydrolysis reaction under the action of acid and deprotection of ethylene glycol, to obtain the compound of formula (8);
- (f) in the sixth solvent, under the action of catalyst and hydrogen under pressure, the compound in formula (8) is heated with alkali and subjected to reduction and hydrolysis reaction, to obtain ursodeoxycholic acid shown in formula (9);
- or, the said method comprises the following steps:
- (g) in the seventh solvent, BA shown in formula (1) is oxidized to obtain the compound of formula (4);
- (h) in the eighth solvent, the compound formula (4) undergoes Wittig reaction to obtain the compound formula (5);
- (i) in the ninth solvent, the compound of formula (5) is protected by ethylene glycol or neopentyl glycol to obtain the compound of formula (6);
- (d) in the fourth solvent, the compound of formula (6) is oxidized to obtain the compound of formula (7);
- (e) in the fifth solvent, the compound of formula (7) undergoes hydrolysis reaction under the action of acid and deprotection of ethylene glycol or neopentyl glycol, to obtain the compound of formula (8);
- (f) in the sixth solvent, under the action of catalyst and hydrogen under pressure, the compound of formula (8) is heated with alkali and subjected to reduction and hydrolysis reaction, to obtain the ursodeoxycholic acid as shown in formula (9);
- wherein, the reaction process of the said method is shown in the route (A):
- in the said route (A), R is an alkyl group;
- R1 is
Compounds have the structures shown in formula (6′), formula (6″), formula (7′), formula (7″) or formula (8) respectively:
- wherein R is an alkyl group.
Dependencies are inferred from the claim text.