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17 alpha-acetoxy-6-methylenepregn-4-ene-3,20-dione preparation method

A technology of methylene pregnan and acetoxy is applied in the field of medicine and chemical industry, which can solve the problems of poor reaction selectivity, large amount of waste liquid, large amount of material, etc., and achieves reduction of side reactions, small reaction volume, and continuous production process. Effect

Inactive Publication Date: 2019-12-20
台州仙琚药业有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0006] The purpose of the present invention is to overcome the problems of large amount of online reaction materials, poor reaction selectivity and large amount of waste liquid in the production process of current 17α-acetoxy-6-methylenepregn-4-ene-3,20-dione technical problem

Method used

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  • 17 alpha-acetoxy-6-methylenepregn-4-ene-3,20-dione preparation method

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Embodiment 1

[0026] according to figure 1 In the process flow shown, 17α-hydroxyprogesterone acetate (100mmol, 37.2g), p-toluenesulfonic acid (2mmol, 0.34g) and 300mL tetrahydrofuran were formulated into solution A and placed in a 1L single-port reaction flask; Ethyl ester (120mmol, 17.8g) was dissolved in 100mL ethanol to form solution B, and placed in a 500mL single-necked flask. The materials of solution A and solution B are transported through the metering pump respectively, enter the first mixer for mixing, and adjust the flow through the metering pump to make the 17α-hydroxyprogesterone acetate, p-toluenesulfonic acid and triethyl orthoformate in the mixer The molar flow ratio of the ester is 1:0.02:1.2. The mixed solution in the first mixer enters the first tubular reactor for etherification reaction at 25°C. After staying in the tubular reactor for 0.5h, the ether The reacted material flows out from the first tubular reactor.

[0027] Mix N-methylaniline (120mmol, 12.9g) with 9mL...

Embodiment 2

[0033] according to figure 1 In the process flow shown, 17α-hydroxyprogesterone acetate (100mmol, 37.2g), p-toluenesulfonic acid (5mmol, 0.86g) and 350mL tetrahydrofuran were formulated into solution A and placed in a 1L single-port reaction flask; Ethyl ester (150mmol, 22.2g) was dissolved in 120mL ethanol to form solution B, and placed in a 500mL single-necked flask. The materials of solution A and solution B are transported through the metering pump respectively, enter the first mixer for mixing, and adjust the flow through the metering pump to make the 17α-hydroxyprogesterone acetate, p-toluenesulfonic acid and triethyl orthoformate in the mixer The molar flow ratio of the esters is 1:0.05:1.5, and the mixed liquid in the first mixer enters the first tubular reactor for etherification reaction at 30°C, stays in the tubular reactor for 45 minutes, and etherifies The reacted material flows out from the first tubular reactor.

[0034] Mix N-methylaniline (100mmol, 10.7g) wi...

Embodiment 3

[0037] according to figure 1 In the process flow shown, 17α-hydroxyprogesterone acetate (100mmol, 37.2g), pyridinium p-toluenesulfonate (2mmol, 0.5g) and 300mL tetrahydrofuran were formulated into solution A and placed in a 1L single-port reaction flask; Triethyl formate (200mmol, 29.6g) was dissolved in 120mL ethanol to form solution B, and placed in a 500mL single-necked flask. The materials of solution A and solution B are conveyed by metering pumps respectively, enter the first mixer for mixing, and adjust the flow through the metering pump to make the 17α-hydroxyprogesterone acetate, pyridinium p-toluenesulfonate and orthoformic acid entering the mixer The molar flow ratio of triethyl ester is 1:0.02:2, and the mixed solution in the first mixer enters the first tubular reactor for etherification reaction at 30°C, and stays in the tubular reactor for 30 minutes. The material after the etherification reaction flows out from the first tubular reactor.

[0038] Diphenylamin...

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Abstract

The invention discloses a 17 alpha-acetoxy-6-methylenepregn-4-ene-3,20-dione preparation method, which comprises: carrying out an etherification reaction, a Mannich reaction and an elimination reaction on 17 alpha-hydroxyprogesterone acetate represented by a formula (I) and used as an initial raw material in a tubular reactor to obtain a product 17 alpha-acetoxy-6-methylenepregn-4-ene-3,20-dione represented by a formula (II), wherein the reaction formula is defined in the specification. According to the present invention, by using the tubular reaction mode approximate to plug flow, the materials are hardly backmixed during the reaction, the mass transfer and heat transfer efficiency is good, the generation of side reactions is remarkably reduced, and the method has advantages of high product yield, high product purity, easy operation, few three-waste and the like, and is suitable for industrial production.

Description

technical field [0001] The invention relates to a preparation method of a key intermediate of medroxyprogesterone acetate, 17α-acetoxy-6-methylenepregna-4-ene-3,20-dione, which belongs to the technical field of medicine and chemical industry. Background technique [0002] 17α-Acetoxy-6-methylenepregna-4-ene-3,20-dione is an important intermediate in the synthesis of steroid hormone medroxyprogesterone acetate. Clinically, medroxyprogesterone acetate can be used not only for the treatment of dysmenorrhea, irregular menstruation and threatened miscarriage, but also for the adjuvant treatment of tumors including breast cancer, kidney cancer and prostate cancer. [0003] The preparation methods of 17α-acetoxy-6-methylenepregna-4-ene-3,20-dione can be mainly divided into the following two types: the first one is to introduce formyl group at the 6-position by Vilsmier reaction, and 6-position hypomethylation is achieved by reduction (eg, Tetrahedron, 1964, 20:597-609; Chem. Pharm...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07J7/00B01J19/24B01J4/02
CPCB01J4/02B01J19/242C07J7/0045
Inventor 潘建洪顾光志陈凯
Owner 台州仙琚药业有限公司
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