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Method for efficient separation and recycling of epoxy isomer in telapristone synthesis

A telapristone and isomer technology, applied in the field of efficiently obtaining 5,10-α epoxy isomers in the synthesis process of telapristone, can solve the problems of coma, volatile, flammable and explosive, etc. , to achieve the effects of improving utilization efficiency, convenient operation, excellent yield and purity

Inactive Publication Date: 2017-09-26
EAST CHINA NORMAL UNIVERSITY
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Ethyl ether is extremely volatile, flammable and explosive, high concentration of ether can cause coma, and the mixed solvent is not suitable for effective recovery

Method used

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  • Method for efficient separation and recycling of epoxy isomer in telapristone synthesis
  • Method for efficient separation and recycling of epoxy isomer in telapristone synthesis
  • Method for efficient separation and recycling of epoxy isomer in telapristone synthesis

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0047] Example 1: Synthesis and separation of epoxy isomer 5,10-α / β

[0048] In a 1000mL three-neck flask equipped with a thermometer, a constant pressure titration funnel, and a glass stopper, add 17β-cyano-17α-trimethylsilyloxy-13β-methylsterane-5,9-diene-3, 3-(Ethylenedioxy) (52.2g, 0.117mol), add 300mL of dichloromethane, stir vigorously for 20min to dissolve the material completely, add disodium hydrogen phosphate (18.1g, 0.127mol), hexafluoroacetone (2.26 mL, 0.0252mol), it was placed in an ice-salt bath and continued to stir for 20 min, and slowly added 30% H 2 o 2 (73.0mL, 0.643mol), after the reaction is stable without exothermic heat, it can be placed at room temperature and continue to stir vigorously. After 24 hours of reaction, TLC detects that the reaction is complete. Slowly add 50mL saturated sodium thiosulfate, stir for 1h, let stand to separate the layers, separate the organic phase, and use saturated Na 2 SO 4 , saturated NaHCO 3 , saturated NaCl to was...

Embodiment 2

[0050] Embodiment 2: the reduction recycling of mother liquor

[0051] Take 20 g of the above-mentioned concentrated mother liquor and place it in a 100 mL single-necked bottle, dissolve it in 100 mL THF, stir and dissolve under an ice bath, add a reducing agent (70 mmol), maintain the system temperature and stir for 2 h, after TLC detects that the reaction is complete, add 2% paraffin Aqueous toluenesulfonic acid solution (20mL), stirred for 30min, then added 200mL dichloromethane and allowed to stand for stratification, and the organic phase was sequentially washed with 20mL saturated NaHCO 3 , washed the organic phase with 20 mL saturated NaCl, anhydrous NaCl 2 SO 4 Dry, filter, and concentrate under reduced pressure to obtain 12.5 g of 17β-cyano-17α-trimethylsilyloxy-13β-methylsterane-5,9-diene-3,3-(ethylenedioxy) , the yield was 65%. 1 H NMR (400MHz, CDCl 3 )δ5.62(t,J=4Hz,1H),3.98(s,4H),2.57-0.79(m,18H),0.89(s,3H),0.23(s,9H). 13 C NMR (100MHz, CDCl 3 ): δ135.88, 130...

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Abstract

The invention discloses a method for efficient separation and recycling of 5,10-alpha epoxy isomer in telapristone synthesis. A 5,10-alpha epoxide is a key intermediate in a telapristone synthesis process, and preparation of a high-purity 5,10-alpha epoxy isomer is the key in control of a whole quality system. The 5,10-alpha isomer is efficiently separated by means of solvent pulping for the first time, the content reaches 99%, and the yield is up to 65%. More significantly, a mixture of two epoxy isomers in mother solution after separation of the 5,10-alpha epoxy isomer can be subjected to reduction and elimination reaction to return to a raw material 17beta-cyano-17alpha-trimethylsiloxy-13beta-methyl sterane-5,9-diene-3,3-(ethylenedioxy). The method is remarkable in improvement of raw material utilization efficiency and has a large-scale application prospect.

Description

technical field [0001] The invention belongs to the technical field of chemistry, and relates to a method for separating organic chiral compounds and a mother liquor recycling method, in particular to a method for efficiently obtaining 5,10-α epoxy isomers in the synthetic process of telapristone and a mother liquor recycling method method. Background technique [0002] Telapristone developed by Repros is a typical drug candidate as a selective progesterone receptor, and is in Phase III clinical trials (Barbara J.Attardi, Janet Burgenson, Sheri A.Hild, Journal of Steroid Biochemistry & Molecular Biology, 2004, 88, 277–288). 5α,10α-epoxide is a key intermediate in the synthetic process of telapristone, and also a key intermediate in the quality control of the whole process. During the epoxidation reaction of 17β-cyano-17α-trimethylsilyloxy-13β-methylsterane-5,9-diene-3,3-(ethylenedioxy) 5,10-α / β Epoxides in two configurations, as shown in the following formula. The ratio ...

Claims

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Application Information

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IPC IPC(8): C07J71/00C07J21/00
CPCC07J21/006C07J71/001
Inventor 汤杰李念潘娜管凤洁阮礼波杨帆于丽芳
Owner EAST CHINA NORMAL UNIVERSITY
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