Method for preparing abiraterone acetate without heavy-metal residue
A technology of abiraterone acetate and acid-binding agent, which is applied in the production of steroids, bulk chemicals, organic chemistry, etc., can solve the problems of unsuitability for large-scale production, harsh operation methods, unfavorable material preparation and operation, etc., and achieve good Prospect of industrial application and effect of cost reduction
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[0045] Example 1 Synthesis of Abiraterone Acetate
[0046] (1) Protection of hydroxyl
[0047] Dissolve 10.0 g of dehydroepiandrosterone in 80 ml of THF, add 3.5 g of 3,4-dihydro-2H-pyran (DHP) under stirring at room temperature, and add 0.5 ml of trifluoroacetic acid as a catalyst. The reaction solution is stirred at room temperature for 10- 12h.
[0048] The reaction solution was desolventized under reduced pressure, the residue was dissolved in 100ml water and 100ml ethyl acetate, and the layers were separated. The aqueous phase was extracted twice with 50ml of ethyl acetate each time. The ethyl acetate phases were combined and washed once with 150ml of water. Washed with 150ml saturated brine once, dried with anhydrous sodium sulfate and desolubilized to obtain 11.5g of product (yield 89%), without purification, it can be used directly in the next reaction.
[0049] (2) Aldol reaction
[0050] Dissolve 10.0 g of THP-protected dehydroepiandrosterone in 50 ml of THF after anhydrous ...
Example Embodiment
[0061] Example 2 Synthesis of Abiraterone Acetate
[0062] (1) Protection of hydroxyl
[0063] Dissolve 10.0 g of dehydroepiandrosterone in 80 ml of THF, add 4.5 g of trimethylchlorosilane (TMSCl) under stirring at room temperature, and add 7.5 ml of triethylamine as an acid binding agent, and stir the reaction solution at room temperature for 10-12 hours.
[0064] The reaction solution was desolventized under reduced pressure, the residue was dissolved in 100ml water and 100ml ethyl acetate, and the layers were separated. The aqueous phase was extracted twice with 50ml of ethyl acetate each time. The ethyl acetate phases were combined and washed once with 150ml of water. Washed with 150ml of saturated brine once, dried with anhydrous sodium sulfate and desolventized to obtain 12.1g of product (yield 97%), without purification, it can be used directly in the next reaction.
[0065] (2) Aldol reaction
[0066] Dissolve 10.0 g of THP-protected dehydroepiandrosterone in 50 ml of THF after...
Example Embodiment
[0077] Example 3 Synthesis of Abiraterone Acetate
[0078] (1) Protection of hydroxyl
[0079] Dissolve 10.0 g of dehydroepiandrosterone in 80 ml of DMF, add 6.3 g of trimethylchlorosilane (TBSCl) under stirring at room temperature, and add 3.3 g of imidazole as an acid binding agent, and stir the reaction solution for 10-12 hours at room temperature.
[0080] The reaction solution was poured into 100ml water, the phase was extracted three times with 50ml of ethyl acetate each time, the ethyl acetate phases were combined, washed once with 150ml of water, washed once with 150ml of saturated brine, dried with anhydrous sodium sulfate and desolventized to obtain 13.5g of crude product, quickly purified using thin-layer silica gel cake to obtain 12.8g (92% yield), which can be used in the next reaction.
[0081] (2) Aldol reaction
[0082] Dissolve 12.0 g of THP-protected dehydroepiandrosterone in 50 ml of THF after anhydrous treatment, and pre-cool for use.
[0083] Dissolve 5.2 g of 3-bro...
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