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ChemicalBook CAS DataBase List Abiraterone acetate

Abiraterone acetate synthesis

6synthesis methods
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
  • 202112070538584790.jpg

    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).

  • ROUTE 2
  • 202112075118991875.jpg

    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).

  • ROUTE 3
  • 202112075909006204.jpg

    Li, Zhenfei; Alyamani, Mohammad; Li, Jianneng; Rogacki, Kevin; Abazeed, Mohamed; Upadhyay, Sunil K.; Balk, Steven P.; Taplin, Mary-Ellen; Auchus, Richard J.; Sharifi, Nima. Redirecting abiraterone metabolism to fine-tune prostate cancer anti-androgen therapy. Nature (London, United Kingdom). Volume 533. Issue 7604. Pages 547-551. Journal; Online Computer File. (2016).

  • ROUTE 4
  • 202112078187395196.jpg

    Li, Yaling; Wang, Shuli. Method for synthesizing Abiraterone acetate. Assignee Tianjin Kingyork Group Co., Ltd., Peop. Rep. China. CN 104558091. (2015).

  • ROUTE 5
  • 202112077974228105.jpg

    Xie, Zhixiang; Guo, Yueming. Method for preparing Abiraterone acetate. Assignee Lanzhou University, Peop. Rep. China. CN 105622703. (2016).

  • ROUTE 6
  • 202112072163559957.jpg

    Kuo, Lung-Huang; Fang, Hsiao-Ping; Wu, Ming-Feng; Chang, Yu-Sheng. Process for the preparation of abiraterone and intermediates thereof. Assignee ScinoPharm Taiwan, Ltd., Taiwan; ScinoPharm Singapore Pte, Ltd. WO 2014207567. (2014).

  • ROUTE 7
  • 202112072791400575.jpg

    Marom, Ehud; Rubnov, Shai; Mizhiritskii, Michael. Process and intermediates for the preparation of abiraterone acetate. Assignee Mapi Pharma Ltd., Israel. WO 2014016830. (2014).

202112070538584790.jpg

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).

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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

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