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A kind of synthetic method of 3α-hydroxyl-5α-cholanic acid

A synthesis method and technology of cholanoic acid, applied in the direction of steroids, organic chemistry, etc.

Active Publication Date: 2021-09-10
HEZE RUIZHI TECH DEV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Since the 3α-hydroxyl-5α-cholanic acid isomer of lithocholic acid can be applied to the synthesis of other similar steroidal compound derivatives, and the 3α-hydroxyl-5α-cholanic acid isomer of lithocholic acid has a significant effect on the synthesis of lithocholic acid. The safety of use is of great significance, but there are few reports about the synthesis method of 3α-hydroxyl-5α-cholanic acid in the prior art. Therefore, it is possible to design a method that can stably obtain 3α-hydroxyl-5α-cholanic acid The method of synthesis is very important

Method used

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  • A kind of synthetic method of 3α-hydroxyl-5α-cholanic acid
  • A kind of synthetic method of 3α-hydroxyl-5α-cholanic acid
  • A kind of synthetic method of 3α-hydroxyl-5α-cholanic acid

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Experimental program
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Effect test

Embodiment 1

[0038] One, the synthesis of formula (2) compound

[0039] Take 10 g of hyodeoxycholic acid (25.5 mmol), add 100 mL of methanol, then cool down to 5 °C, add 0.5 mL of concentrated sulfuric acid dropwise within about 10 min, stir until the solid dissolves, raise to 25 °C, and stir for 8 h , HPLC detection showed that the reaction was complete, then adding 100 mL of saturated sodium bicarbonate solution to quench the reaction, concentrating under reduced pressure, extracting with 150 mL of ethyl acetate, combining the organic phases, followed by 2*150 mL of saturated sodium bicarbonate, 3*100 Wash with mL of saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate under reduced pressure to obtain 10.4 g of a white solid with a molar yield of 100%. 1 H-NMR (400 MHz, CDCl 3 / TMS): δ = 0.66 (3H, 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).

[0040] Two, the synthesis of formula (3) compound

[0041] Take 10 g of...

Embodiment 2

[0048] One, the synthesis of formula (2) compound

[0049] 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%.

[0050] Two, the synthesis of formula (3) compound

[0051] 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 synthesis method of 3α-hydroxy-5α-cholanic acid. The present invention uses hyodeoxycholic acid as a starting material, and undergoes 4 steps of 24-carboxyl esterification, 3α-OH and 6α-OH oxidation to carbonyl, selective reduction, and Huang Minglong reaction to generate lithocholic acid isomer 3α-hydroxyl -5α-cholic acid fills the gap in the field of lithocholic acid isomer synthesis, and the method of the present invention can stably obtain the lithocholic acid isomer, namely 3α-hydroxyl-5α-cholanic acid, wherein The total yield of lithocholic acid isomers, namely 3α-hydroxy-5α-cholanic acid, was as high as 47%.

Description

technical field [0001] The invention relates to the technical field of organic synthesis, in particular to a synthesis method of 3α-hydroxyl-5α-cholanic 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] In 1946, Journal of Biological Chemistry, 1946, 162, 555-563 reported that deoxycholic acid was used as the starting material, after methylation, hydroxyl double protection, and then selective removal of 3-OH protecting group, hydrolysis, and hydrogenation through seven steps of reaction synthesis Lithocholic acid....

Claims

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Application Information

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Patent Type & Authority Patents(China)
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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