Synthesis method of ursodesoxycholic acid
The technology of a kind of ursodeoxycholic acid and its synthesis method is applied in the field of ursodeoxycholic acid synthesis, which can solve the problems of unsuitability for large-scale industrial production, high synthesis cost, and low yield, and achieve high synthesis cost and side effects. The effect of less reaction and high yield
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Embodiment 1
[0088] Preparation of compound shown in embodiment 1 formula (II)
[0089] This embodiment provides the preparation method of the compound shown in formula (II), specifically any one of the following 1-3:
[0090] 1. In a 500 ml reaction flask, add 7β-OH-4-HBC (10 g, 28.86 mmol), maleic anhydride (6 g, 61.19 mmol), 40 ml of acetone, dimethylamine (4.2 g, 93.17 mmol), 2,6-Lutidine (0.2 g, 1.87 mmol). The temperature was raised to 38-40°C, and stirring was maintained at this temperature for 5 hours. After detecting the completeness of the reaction by TLC, the acetone was removed by concentration under reduced pressure, 30 ml of water was added, and the temperature was lowered to 20°C. 10% hydrochloric acid was added dropwise to adjust the pH to 3.5-4.0, and turbidity appeared. 30 ml of methanol was added, and crystallization occurred. Filter, wash with water twice, dry to obtain white to off-white solid powder (10.81 grams, 27.61mmol), be the compound shown in formula (II), ...
Embodiment 2
[0095] Preparation of the compound shown in embodiment 2 formula (III)
[0096] This embodiment provides the preparation method of the compound represented by formula (III), specifically any one of the following 1-3:
[0097] 1. In a 500 ml reaction flask, add the compound (10 g, 24.84 mmol) represented by formula (II), 50 ml tetrahydrofuran, and stir for 30 minutes at 25-30 ° C until the compound represented by formula (II) is completely dissolved . Add N-bromosuccinimide NBS (5.2 g, 29.22 mmol), and continue stirring at 10° C. for 4 hours to obtain an off-white suspension. As detected by TLC, the reaction was complete, and concentrated under reduced pressure to remove tetrahydrofuran. Add water, filter with suction, extract with dichloromethane three times, wash with water twice, concentrate under reduced pressure, and purify by silica gel column chromatography (PE / EA=3 / 1, v / v) to obtain the compound (9.2 g, 22.91 mmol), after calculation, the mass yield of the compound r...
Embodiment 3
[0101] Preparation of the compound shown in embodiment 3 formula (IV)
[0102] This embodiment provides the preparation method of the compound shown in formula (IV), specifically any one of the following 1-3:
[0103] 1, in a 500 milliliter reaction bottle, add the compound (2 grams, 4.98mmol) shown in formula (III), ethoxyformyl methylene triphenylphosphine (4.12g, 11.83mmol), tetrahydrofuran 30ml, 0 Reflux reaction at -4°C for 4h. Concentrate under reduced pressure after the TLC detection reaction is complete, silica gel column chromatography (PE / EA=3 / 1, v / v) purify, obtain the compound (2.2g, 4.68mmol) shown in formula (IV), through calculating formula (IV ) The mass yield of the compound shown in ) is 110%, and the molar yield is 93.97%.
[0104] 2, in a 500 milliliter reaction bottle, add the compound (2 grams, 4.98mmol) shown in formula (III), ethoxyformyl methylene triphenylphosphine (2.12g, 6.09mmol), tetrahydrofuran 30ml, 0 Reflux reaction at -4°C for 4h. Concentr...
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