Check patentability & draft patents in minutes with Patsnap Eureka AI!

Preparation method of ulipristal acetate key intermediate

A technology of uliplast acetate and intermediates, which is applied in the field of compound preparation, can solve the problems of high waste water post-treatment cost, wide fluctuation range of yield, poor reaction stability, etc., and achieve broad industrial application prospects, stable process and high product quality. Effect of Yield Improvement

Active Publication Date: 2013-06-12
ZHEJIANG XIANJU PHARMA
View PDF5 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The disadvantage is that the steps are long, and the third step reaction uses trimethyl phosphite with a strong smell as a reaction reagent, and the water is used to precipitate the material when discharging, which is relatively large to air pollution and the post-treatment cost of waste water is also high; in addition , the reaction stability of the fourth step is poor, and the yield fluctuation range is wide

Method used

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
View more

Image

Smart Image Click on the blue labels to locate them in the text.
Viewing Examples
Smart Image
  • Preparation method of ulipristal acetate key intermediate
  • Preparation method of ulipristal acetate key intermediate
  • Preparation method of ulipristal acetate key intermediate

Examples

Experimental program
Comparison scheme
Effect test

preparation example Construction

[0030] The preparation method of the key intermediate of uliplast acetate of the present invention adopts the chemical formula of 3-(ethylenedioxy)-21-(phenyl-sulfinyl)-19-desmethylpregna-5 (10), 9(11), 17(20), 20-tetraene as the starting material, in a reaction tank, use a one-pot method to complete the three-step reaction to obtain the general structure shown in formula I or formula II The compound, which is a structurally similar bisketal compound, is an equivalent intermediate in chemical synthesis;

[0031]

[0032]

[0033] Specifically include the following steps:

[0034] In the first step, 3-(ethylenedioxy)-21-(phenyl-sulfinyl)-19-desmethylpregna-5(10), 9(11), 17(20), 20-tetraene reacts with alcohol;

[0035] In the second step, the reaction solution obtained in the first step is reacted with phosphite to obtain an enol ether compound;

[0036] In the third step, acid is added to the reaction liquid obtained in the second step, and the reaction is stirred at ...

Embodiment 1

[0051] Embodiment 1: the synthesis of compound 1

[0052] Under the protection of nitrogen, add 120ml of methanol and 0.48g of sodium methoxide into the three-necked flask, and stir well; add 20g of 3-(ethylenedioxy)-21-(phenyl-sulfinyl)-19-desmethylpregnan Steroid-5(10), 9(11), 17(20), 20-tetraene, keep warm at 20-25°C and stir for 24 hours, then add 5.5ml trimethyl phosphite, keep warm at 53-57°C and stir for reaction 3 After 1 hour, 2ml of phosphoric acid was added and stirred; after 60 minutes, the reaction was complete; the temperature was lowered to 3°C, and filtered; the filter cake was rinsed with 20ml of methanol; after drying, 12g of compound 1 was obtained.

Embodiment 2

[0053] Embodiment 2: the synthesis of compound 2

[0054] Add 120ml of ethanol and 0.48g of sodium methoxide into a three-necked flask, stir well, add 20g of 3-(ethylenedioxy)-21-(phenyl-sulfinyl)-19-desmethylpregna-5 ( 10), 9(11), 17(20), 20-tetraene, heat up to 38-40°C and stir for reaction; after 16 hours, add 12ml of triethyl phosphite, keep warm at 54-56°C and stir for reaction; after 3 hours , cooled to room temperature; added 1.4ml of trifluoromethanesulfonic acid and stirred; after 55 minutes, cooled to 0°C and filtered; the filter cake was rinsed with 20ml of ethanol; after drying, 12.68g of compound 2 was obtained.

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

PUM

No PUM Login to View More

Abstract

The invention discloses a preparation method of ulipristal acetate key intermediate. The preparation method comprises the following steps of: utilizing 3-(ethylenedioxy)-21-(phenyl-sulfinyl)-19-demethyl pregnane-5(10),9(11),17(20),20-tetraene as an initiator, and finishing three reaction steps in a reaction tank through a one-pot method to prepare a compound with a structural general formula expressed by formula I or formula II. The preparation method disclosed by the invention can avoid the intermediate discharge process, three discharge steps and four reaction steps are respectively changed into one integrated discharge step and three reaction steps, so that the process route is greatly shortened, and meanwhile, the technique is stable, the operation is simple, the yield of the product is greatly improved to be higher than 60%, and the product purity is high, so that the preparation method has an extensive industrial application prospect.

Description

technical field [0001] The invention relates to a preparation method of a compound, in particular to a preparation method of a key intermediate of uliplast acetate. Background technique [0002] Ulipristal acetate, English name Ulipristal acetate, chemical name 17α-(acetyloxy)-11β-[4-(N,N-dimethylamino)phenyl]-19-norpregna-4,9 -diene-3,20-dione, which is mainly used for emergency contraception within 120 hours of unprotected intercourse or contraceptive failure. In addition to being used for emergency contraception, the compound has other gynecological indications, and the drug has been approved for marketing in Europe and the United States. [0003] The bisketal is one of the key intermediates for the synthesis of CDB-2914, and its structural formula is as follows: [0004] [0005] At present, there are two routes for the synthesis of compound bisketals. The first route was published in Steroids in 2000 by Pemmaraju N.Rao, as follows: [0006] [0007] The second ...

Claims

the structure of the environmentally friendly knitted fabric provided by the present invention; figure 2 Flow chart of the yarn wrapping machine for environmentally friendly knitted fabrics and storage devices; image 3 Is the parameter map of the yarn covering machine
Login to View More

Application Information

Patent Timeline
no application Login to View More
Patent Type & Authority Applications(China)
IPC IPC(8): C07J21/00
Inventor 李卫鹏
Owner ZHEJIANG XIANJU PHARMA
Features
  • R&D
  • Intellectual Property
  • Life Sciences
  • Materials
  • Tech Scout
Why Patsnap Eureka
  • Unparalleled Data Quality
  • Higher Quality Content
  • 60% Fewer Hallucinations
Social media
Patsnap Eureka Blog
Learn More

Browse by: Latest US Patents, China's latest patents, Technical Efficacy Thesaurus, Application Domain, Technology Topic, Popular Technical Reports.

© 2025 PatSnap. All rights reserved.Legal|Privacy policy|Modern Slavery Act Transparency Statement|Sitemap|About US| Contact US: help@patsnap.com