ChemicalBook CAS DataBase List Abiraterone acetate

Abiraterone acetate synthesis

6synthesis methods

Product Name:Abiraterone acetate
CAS Number:154229-18-2
Molecular formula:C26H33NO2
Molecular Weight:391.55

Abiraterone acetate is an FDA approved drug, and is an orally active acetate ester of the steroidal compound abiraterone with antiandrogen activity. Abiraterone acetate was approved by the U.S. Food and Drug Administration (FDA) in April 2011. Abiraterone inhibits the enzymatic activity of steroid 17alpha-monooxygenase (17alpha-hydrolase/C17,20 lyase complex), a member of the cytochrome p450 family that catalyzes the 17alpha-hydroxylation of steroid intermediates involved in testosterone synthesis. Administration of this agent may suppress testosterone production by both the testes and the adrenals to castrate-range levels. FDA Approval this drug in May 2011.

Synthetic Routes

ROUTE 1

ROUTE 2

ROUTE 3

ROUTE 4

ROUTE 5

ROUTE 6

ROUTE 7

Madhra, Mukesh Kumar; Sriram, Hari Mohan; Inamdar, Murad; Sharma, Mukesh Kumar; Prasad, Mohan; Joseph, Sony. Improved Procedure for Preparation of Abiraterone Acetate. Organic Process Research & Development. Volume 18. Issue 4. Pages 555-558. Journal; Online Computer File. (2014).

108-24-7
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154229-19-3 Synthesis

154229-19-3
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154229-18-2
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Yield:154229-18-2 96.7%

Reaction Conditions:

with triethylamine in dichloromethane at 0 - 20; for 3 h;

Steps:

2; 3; 4

6.4 g (0.018 mol) of abiraterone, 50 mL of dichloromethane, and 3.0 g (0.03 mol) of triethylamine were added to the reaction flask. The temperature was lowered to 0-5°C, and 3.0 g (0.03 mol) of acetic anhydride was slowly added dropwise. After dropping, the temperature was raised to room temperature, and maintain temperature reaction for 3 hours. Filter and wash the organic layer once with 20 mL of water, 20 mL of 1 N aqueous sodium bicarbonate solution. The organic layer was concentrated to dryness under reduced pressure, 20 mL of 90% ethanol aqueous solution was added to the concentrate, and the temperature was raised to reflux to make the solution clear. The temperature was lowered to 0-5° C. for two hours, crystallized, filtered, and dried in vacuo to obtain 6.8 g of crude abiraterone acetate with a molar yield of 96.7% and HPLC purity of 98.3%. The crude product was recrystallized with acetone to obtain 6.2 g of abiraterone acetate with a purity of 99.6%.

References:

CN114853838,2022,A Location in patent:Paragraph 0092-0093; 0096; 0097-0098; 0101; 0102-0103; 0106