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A method for synthesizing lithocholic acid from hyodeoxycholic acid

A technology of hyodeoxycholic acid and lithocholic acid, which is applied in the directions of steroids, organic chemistry, etc., can solve the problems of low yield, cumbersome post-processing and high cost, and achieves good selectivity, novel method and safe synthesis process conditions. Effect

Active Publication Date: 2021-06-22
HEZE RUIZHI TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0006] In this synthetic route, an expensive platinum dioxide catalyst is used, and the yield is only 23%. The cost is high and the yield is low, which limits the industrial production
[0007] Although CN106977572A discloses a method for synthesizing lithocholic acid using hyodeoxycholic acid as a raw material, a method for synthesizing lithocholic acid is disclosed in two steps, but in this patent, hydrazine hydrate is used when Huang Minglong reduction reaction is carried out, because Hydrazine hydrate is a highly toxic reagent, and it is easy to explode when the temperature is high, and the aftertreatment brought by the use of hydrazine hydrate is very tedious and not environmentally friendly. , the demand for safe production, it is difficult to carry out industrial production

Method used

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  • A method for synthesizing lithocholic acid from hyodeoxycholic acid
  • A method for synthesizing lithocholic acid from hyodeoxycholic acid
  • A method for synthesizing lithocholic acid from hyodeoxycholic acid

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Embodiment 1

[0037] One, the synthesis of formula (2) compound

[0038] Take 100 g of hyodeoxycholic acid (255 mmol), add 1000 mL of methanol, then cool down to 5°C, add 5mL of concentrated sulfuric acid drop by drop, stir until the solid dissolves, rise to 25°C, stir for 8 hours, HPLC detects that the reaction is complete, Then add 1000 mL of saturated sodium bicarbonate solution to quench the reaction, concentrate under reduced pressure, extract with 1500 mL of ethyl acetate, combine the organic phases, wash with 2*1500 mL of saturated sodium bicarbonate, 3*1000 mL of saturated brine, and anhydrous Dry over sodium sulfate, filter, and concentrate under reduced pressure to obtain 104 g of a white solid with a molar yield of 100%. 1 H NMR (400 MHz, CDCl 3 / TMS): δ = 0.66 (3 H, s, 18-H), 0.94 (6 H, t, J = 1.4 Hz), 3.63 (1 H, m, 6α-H), 3.69 (3 H, s) , 4.07 (1H, m,3α-H).

[0039] Two, the synthesis of formula (3) compound

[0040] Take 100 g of the compound of formula (2), add 1000 mL of ...

Embodiment 2

[0053] One, the synthesis of formula (2) compound

[0054] Take 10 g of hyodeoxycholic acid, add 100 mL of methanol, then cool down to 0°C, add 0.5mL of concentrated sulfuric acid dropwise within about 10 minutes, stir until the solid dissolves, rise to 25°C, stir for 12 hours, and detect the reaction by HPLC complete, then add 100 mL of saturated sodium bicarbonate solution to quench the reaction, concentrate under reduced pressure, extract with 150 mL of ethyl acetate, and wash the organic phase with 2*150 mL of saturated sodium bicarbonate and 3*100 mL of saturated brine, respectively. Dry over sodium sulfate, filter, and concentrate to obtain 10.0 g of white solid, with a molar yield of 96.6%.

[0055] Two, the synthesis of formula (3) compound

[0056] Take 10 g of the compound of formula (2), add 200 mL of dichloromethane, stir at room temperature to dissolve, add 16 g of oxidant PCC, react for 20 min after the dropwise addition, TLC detection shows that the reaction is...

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Abstract

The invention discloses a method for synthesizing lithocholic acid by using hyodeoxycholic acid as a raw material. The present invention uses hyodeoxycholic acid as a starting material, undergoes 7 steps of 24-carboxyl esterification, 3α-hydroxyl and 6α-hydroxyl oxidation to carbonyl, selective reduction, acylation, hydrazone formation, dehydrazone, and hydrolysis to form stones. cholic acid. The starting material of the invention is cheap and easy to obtain, hydrazine hydrate is not used in the synthesis process, the synthesis process conditions are safe, environmentally friendly and mild, the total yield is high, and the method is suitable for industrial production.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a method for synthesizing lithocholic acid from hyodeoxycholic acid. Background technique [0002] Lithocholic acid, named 3α-hydroxy-5β-cholanic acid, is a bile acid present in the bile of humans, cattle, and rabbits, and gallstones of cattle and pigs. Studies have shown that it and its derivatives have various physiological functions. Activity, the effect of inhibiting tumors, such as selectively killing neuroma cells, but has almost no toxicity to normal cells; the change of its content has important reference value in the diagnosis of liver diseases. [0003] [0004] At present, lithocholic acid is mainly derived from the extraction and separation of animal bile, and the chemical synthesis method is rarely reported, which cannot meet the market demand; therefore, it is necessary to develop a novel, practical and industrialized synthesis route. In 1946, Journal ...

Claims

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Application Information

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IPC IPC(8): C07J9/00
CPCC07J9/005
Inventor 韩迎郭彩云刘彦丽王尤汉姚洪董超
Owner HEZE RUIZHI TECH DEV
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