Unlock instant, AI-driven research and patent intelligence for your innovation.

Method for recovering desogestrel recrystallization mother liquor

A technology for desogestrel and recovery methods, applied in chemical instruments and methods, steroids, estrone derivatives, etc., can solve the problems of inability to recover desogestrel, achieve high atomic utilization rate, and improve economic efficiency benefit effect

Pending Publication Date: 2022-02-18
SHANGHAI GONGTUO PHARMA & CHEM IND
View PDF0 Cites 0 Cited by
  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0003] The purpose of the present invention is to solve the problem in the prior art that desogestrel cannot be further recovered by ordinary recrystallization methods when the content ratio of △3 isomer and desogestrel in the crystallization mother liquor reaches 40:60 Shortcoming, and the recovery method of proposed desogestrel recrystallization mother liquor

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
  • Method for recovering desogestrel recrystallization mother liquor
  • Method for recovering desogestrel recrystallization mother liquor
  • Method for recovering desogestrel recrystallization mother liquor

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0028] Example side chain degradation:

[0029] Desogestrel mother liquor (brown oil, dry product, containing 53% desogestrel, 34% △3 isomer and 9% 17-epimer, GC) 30g refer to J.C.S.Chem.Comm.1972, 468 method, obtained brown oil 27.3g (containing 18-methyl-11-methyleneestr-4-en-17-one 57% and 18-methyl-11-methyleneestr-3- En-17-one 37%, GC).

Embodiment 2

[0030] Embodiment two reduction:

[0031] Add 25g of the oily matter obtained in Example 1 to a 1000ml three-neck round-bottomed flask, add 500ml of methanol and stir to dissolve, add a total of 10g of sodium borohydride in batches at room temperature, monitor the reaction process by TLC, acidify with acetic acid after the reaction finishes, evaporate The solvent was removed, water and dichloromethane were added for extraction, and the organic layer was concentrated to dryness to obtain 24.3 g of a brown oil.

Embodiment 3

[0032] Example triesterification:

[0033] Add 120ml of acetic anhydride to the whole amount of the oil obtained in the above reduction step and stir evenly, add 1.2g of p-toluenesulfonic acid into it at room temperature, and monitor the reaction progress by TLC. After the reaction was completed, 2ml of pyridine was added, then poured into 500ml of ice water, and stirred for another 2 hours. After extraction with dichloromethane, the organic layer was washed with water and concentrated to dryness to obtain 26.1 g of a brown oil.

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 belongs to the field of organic chemistry, particularly relates to a method for recovering desogestrel recrystallization mother liquor. In allusion to the problem that desogestrel cannot be further recovered through a common recrystallization method after the content ratio of a [delta]3 isomer to desogestrel in the crystallization mother liquor reaches 40: 60 in the prior art, the invention proposes the following scheme: Side chain degradation, reduction, esterification, bromination, elimination, hydrolysis and Birch reduction are carried out on the recrystallized mother liquor to obtain the desogestrel intermediate with a single component. According to the invention, the desogestrel recrystallization mother liquor is converted into the single-component 18-methyl-11-methylene-estra-4-ene-17beta-ol at high yield, the used main raw material is the original waste mother liquor in desogestrel production, the high atom utilization rate required by environment-friendly production is met, and the economic benefit is improved.

Description

technical field [0001] The invention relates to the technical field of organic chemistry, in particular to a method for recovering desogestrel recrystallization mother liquor. Background technique [0002] Desogestrel is the third-generation progestin, which was first developed by Organon in the Netherlands as an oral contraceptive. There are currently three main synthetic routes to desogestrel (Recueil 1975, 35; Recueil 1988, 331; Tetrahedron 1994, 10709), all of which eventually involve the 3-deoxygenation step, and in this step, it is inevitable to produce A double bond isomer impurity-△3 isomer (ie impurity A in European Pharmacopoeia 9.0 of desogestrel). After various deoxygenation methods have been reported, the content of Δ3 isomer in the deoxygenated crude product is usually in the range of 8-25%. Since the structure and properties of this impurity are very similar to the main product, subsequent purification is difficult and repeated recrystallization is required....

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
IPC IPC(8): C07J1/00
CPCC07J1/007
Inventor 施彬建林晖
Owner SHANGHAI GONGTUO PHARMA & CHEM IND