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Efficient synthesizing method of estriol

A synthesis method and technology of estriol, applied in the direction of steroids, organic chemistry, etc., can solve the problems of easy isomers, etc., and achieve the effects of fast reaction speed, high solid purity, and improved yield and purity

Inactive Publication Date: 2018-05-18
GUANGXI WANDE PHARMA
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The shortcomings of this method are: (1) epoxidation, easy to have isomers; (2) the use of peroxides, there is a great potential safety hazard

Method used

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  • Efficient synthesizing method of estriol
  • Efficient synthesizing method of estriol
  • Efficient synthesizing method of estriol

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Such as figure 1 The efficient synthetic method of described estriol comprises the following steps:

[0026] S1. Add 20g of estrone, 60ml of isopropenyl acetate, and 5g of p-toluenesulfonic acid into the reaction vessel, heat up to reflux for 3 hours, recover 25ml of isopropenyl acetate, then add 20ml of isopropenyl acetate, and continue to keep warm for 2-3 hours , repeatedly recovering part of isopropenyl acetate, and then adding isopropenyl acetate to continue the reaction until no obvious monoester residues were detected by TLC, cooling, adding triethanolamine to adjust pH=9, and suction filtration to obtain brominated reaction intermediates.

[0027] S2. Take 10g of the intermediate to be brominated in the reaction container, add 200ml of ethyl acetate, 3.22g of sodium acetate and 20ml of acetic acid, add 150g of liquid bromine and carry out the bromination reaction at 5°C for 1.5h, and TLC detects that the reaction of the raw materials is complete , Add water to...

Embodiment 2

[0033] Such as figure 1 The efficient synthetic method of described estriol comprises the following steps:

[0034] S1. Add 20g of estrone, 60ml of isopropenyl acetate, and 5g of p-toluenesulfonic acid into the reaction vessel, heat up to reflux for 1 hour, recover 25ml of isopropenyl acetate, then add 20ml of isopropenyl acetate, continue to keep warm for 2 hours, repeat Recover part of isopropenyl acetate, then add isopropenyl acetate to continue the operation of the reaction until TLC detects that there is no obvious monoester compound residue, cool down, add triethanolamine to adjust pH=8, and filter with suction to obtain the product to be brominated. intermediate.

[0035] S2. Take 10g of the intermediate to be brominated in the reaction vessel, add 200ml of ethyl acetate, 3.22g of sodium acetate and 20ml of acetic acid, add 90g of liquid bromine and carry out the bromination reaction at -5°C for 0.5h, and detect the reaction of the raw materials by TLC Completely, aft...

Embodiment 3

[0041] Such as figure 1 The efficient synthetic method of described estriol comprises the following steps:

[0042]S1. Add 20g of estrone, 60ml of isopropenyl acetate, and 5g of p-toluenesulfonic acid into the reaction vessel, heat up to reflux for 2 hours, recover 25ml of isopropenyl acetate, then add 20ml of isopropenyl acetate, and continue to insulate for 2.5 hours. Repeat the operation of recovering part of isopropenyl acetate, and then add isopropenyl acetate to continue the reaction. After TLC detects that there is no obvious monoester residue, cool down, add triethanolamine to adjust pH=8.5, and filter with suction to obtain the bromination reaction intermediates.

[0043] S2. Take 10g of the intermediate to be brominated in the reaction container, add 200ml of ethyl acetate, 3.22g of sodium acetate and 20ml of acetic acid, add 125g of liquid bromine and carry out the bromination reaction at -0°C for 1 hour, and TLC detects that the reaction of the raw materials is co...

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Abstract

The invention provides an efficient synthesizing method of estriol. The method includes the following steps of conducting enolization and acetylation on estrone to obtain a to-be-brominated intermediate, conducting a bromination reaction with the to-be-brominated intermediate as the substrate, ethyl acetate as the solvent and acetic acid / acetate as the buffering solution, adding water for cancellation after the reaction ends, conducting after-extraction treatment operation after layering, recovering the solvent after drying to obtain to-be-hydrolyzed solid, adding DMF for dissolved clarification, conducting a hydrolysis reaction to obtain a hydrolyzed sample, conducting adjustment with acid, conducting suction filtration, and conducting a hydrogenation reaction on a filter cake to obtain estriol. By means of the efficient synthesizing method of estriol, for the phenomenon that isomers easily appear in the estriol synthesis process, the epoxidation process is replaced with bromination,hydrolysis and then reduction, and the synthesizing method has the advantages of being rapid in reaction speed, beneficial for aftertreatment and better in selectivity.

Description

technical field [0001] The invention belongs to the field of hormone synthesis, and in particular relates to a high-efficiency synthesis method of estriol. Background technique [0002] Estriol is a metabolite of estradiol in the body and is a natural estrogen mainly found in urine. Its oral estrogen activity is about 6 times that of estrone, a sex hormone biosynthesis but weaker than estradiol. It is characterized by a selective effect on the vagina and cervical canal, but has no effect on the uterine entity and endometrium. It has a stronger effect on vaginal epithelial keratosis than estradiol, and can promote vaginal mucosal angiogenesis and vaginal epithelial injury healing; at the same time, it can enhance the function of cervical cells and make cervical muscle fibers hyperplasia, thereby increasing the elasticity and softness of the cervix. In addition, it has a feedback inhibitory effect on the hypothalamus and pituitary gland, but does not inhibit ovulation, and o...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J1/00
Inventor 蒋青锋杨正业雷宇
Owner GUANGXI WANDE PHARMA
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