A kind of preparation method of ulipristal acetate key intermediate
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A technology of ulipristal acetate and intermediates, which is applied in the field of medicine, can solve the problems of hidden safety hazards and high concentration of hydrogen peroxide, and achieve the effects of improving safety, reducing severity, and shortening time
Active Publication Date: 2017-09-12
SUZHOU XINENG ENVIRONMENTAL SCI & TECH CO LTD
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[0003] Technical problem to be solved: Aiming at the disadvantages of high concentration of hydrogen peroxide used in the synthesis process of existing ulipristal acetate and potential safety hazards, the present invention provides a key intermediate of ulipristal acetate 3, 3, 20, 20 bis Preparation method of (ethylenedioxy)-17α-hydroxy-5,10-epoxy-19-norpregna-9(11)ene
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Embodiment 1
[0014] A key intermediate of ulipristal acetate 3,3,20,20 bis(ethylenedioxy)-17α-hydroxy-5,10-epoxy-19-norpregna-9(11)ene Proceed as follows:
[0015] Dissolve 1.61 g of 3,3,20,20 bis(ethylenedioxy)-17α-hydroxy-19-norpregna-5(10),9(11) diene in 10 mL of dichloromethane and 40.82 In mL pyridine, add 2.41g of anhydrous magnesium sulfate, ice bath, add 151.89mL of hexachloroacetone and 2.04mL of 30% H 2 o 2 , stirred in an ice bath for 1.5 h, then added 40 mL of dichloromethane and 5.96 g of NaS 2 o 3 ·5H 2 O ice water 30mL, stirred for 30min, separated, extracted once with dichloromethane, washed once, added Na 2 SO 4 Dry, filter and evaporate to dryness to obtain 1.77g of 3,3,20,20 bis(ethylenedioxy)-17α-hydroxy-5,10-epoxy-19-norpregna-9(11)ene .
[0016] Yield of 3,3,20,20 bis(ethylenedioxy)-17α-hydroxy-5,10-epoxy-19-norpregna-9(11)ene prepared in this example 64%.
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Abstract
The invention provides a preparation method of a ulipristal acetate key intermediate 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxy-5,10-epoxy-19-norpregn-9(11)ene. The preparation method comprises the following steps: dissolving 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxy-19-norpregn-5(10),9(11)diene in dichloromethane, carrying out treatment in an ice bath under pyridine conditions, adding anhydrous magnesium sulfate, hexachloroacetone and 30% oxydol, and stirring in the ice bath to react for 1.5 hours, thereby obtaining 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxy-5,10-epoxy-19-norpregn-9(11)ene; and mixing the 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxy-5,10-epoxy-19-norpregn-9(11)ene, sodium-thiosulfate-pentahydrate-containing ice water and dichloromethane to react, and carrying out skimming, extraction, washing, drying, filtration and drying by distillation to obtain the 3,3,20,20-bis(ethylenedioxy)-17alpha-hydroxy-5,10-epoxy-19-norpregn-9(11)ene. The concentration of the oxydol used in the preparation method is 30%, so the potential safety hazard is low.
Description
technical field [0001] The invention belongs to the technical field of medicine, and in particular relates to a key intermediate of ulipristal acetate 3,3,20,20 bis(ethylenedioxy)-17α-hydroxyl-5,10-epoxy-19-normethyl Process for the preparation of pregna-9(11)ene. Background technique [0002] Ulipristal acetate is a potent antiprogestin, during the synthesis, 3,3,20,20 bis(ethylenedioxy)-17α-hydroxy-5,10-epoxy-19-nor Pregnene-9(11)ene is the key intermediate. U.S. Patent US4954490, US5929262, and Chinese Patent 201110339479.8 disclose that in the synthesis route of ulipristal acetate, the raw materials are first synthesized into intermediates 3, 3, 20, and 20 bis( Ethylenedioxy)-17α-hydroxy-19-norpregna-5(10), 9(11) dienes, followed by selective epoxidation with hydrogen peroxide to obtain 3,3,20,20 bis(ethylenedioxy Dioxy)-17α-hydroxy-5,10-epoxy-19-norpregna-9(11)ene, this epoxidation process is an important and key step in the synthesis of ulipristal acetate, the above ...
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Patent Type & Authority Patents(China)
IPC IPC(8): C07J21/00
CPCC07J21/008
Inventor 胡颖陈彦燕张士磊
Owner SUZHOU XINENG ENVIRONMENTAL SCI & TECH CO LTD
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