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ChemicalBook CAS DataBase List Trifluridine
70-00-8

Trifluridine synthesis

12synthesis methods
Trifluridine (also called trifluorothymidine or TFT) is an anti-herpesvirus antiviral drug, used primarily on the eye. It was sold under the trade name, Viroptic, by Glaxo Wellcome, now merged into GlaxoSmithKline. The brand is now owned by Monarch Pharmaceuticals, which is wholly owned by King Pharmaceuticals. It is a nucleoside analogue, a modified form of deoxyuridine, similar enough to be incorporated into viral DNA replication, but the -CF3 group added to the uracil component blocks base pairing. It is a component of the experimental anti-cancer drug TAS-102. Synthetic Description Reference: Fernandez-Lucas, Jesus; Fresco-Taboada, Alba; Acebal, Carmen; Mata, Isabel; Arroyo, Miguel. Applied Microbiology and Biotechnology. Enzymatic synthesis of nucleoside analogues using immobilized 2'-deoxyribosyltransferase from Lactobacillus reuteriVolume. 91. Issue 2. Pages 317-327. Journal; Online Computer File (2011) Synthetic Description Mestre, Jordi; Lishchynskyi, Anton; Castillon, Sergio; Boutureira. Omar. Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived Synthetic Description Referemce: Tanabe, Yoo; Matsuo, Noritada; Ohno, Nobuo. Journal of Organic Chemistry. Direct perfluoroalkylation including trifluoromethylation of aromatics with perfluoro carboxylic acids mediated by xenon difluoride. Volume 53. Issue 19. Pages 4582-5. Journal. (1988) Synthetic Description Reference: Komatsu, Hironori; Umetani, Hideki. Organic Process Research & Development. Synthesis of Trifluorothymidine: Green Glycosylation Condition Using Neither Chloroform nor Transition Metals. Volume 6. Issue 6. Pages 847-850. Journal. (2002) Synthetic Description Liu, Peng; Liu, Wenbo; Li, Chao-Jun. Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light. Journal of the American Chemical Society. Volume 139. Issue 40. Pages 14315-14321. Journal; Online Computer File. (2017). Synthetic Description Wang, Limin; Yu, Gaohui; Yao, Feng; Xiong, Jingjing; Tian, He; Han, Jianwei. Preparation method of trifluridine by esterification, halogenation, reduction, trifluoromethylation of hydroxyl group. Assignee Hongene Biotechnology Ltd., Peop. Rep. China; East China University of Science and Technology. CN 107652341. (2018).
Synthetic Routes
  • ROUTE 1

    • 202112071772836102.jpg

    Reference: Fernandez-Lucas, Jesus; Fresco-Taboada, Alba; Acebal, Carmen; Mata, Isabel; Arroyo, Miguel. Applied Microbiology and Biotechnology. Enzymatic synthesis of nucleoside analogues using immobilized 2'-deoxyribosyltransferase from Lactobacillus reuteriVolume. 91. Issue 2. Pages 317-327. Journal; Online Computer File (2011)

  • ROUTE 2

    • 202112071303364614.jpg

    Mestre, Jordi; Lishchynskyi, Anton; Castillon, Sergio; Boutureira. Omar. Trifluoromethylation of Electron-Rich Alkenyl Iodides with Fluoroform-Derived

  • ROUTE 3

    • 202112075315773024.jpg

    Referemce: Tanabe, Yoo; Matsuo, Noritada; Ohno, Nobuo. Journal of Organic Chemistry. Direct perfluoroalkylation including trifluoromethylation of aromatics with perfluoro carboxylic acids mediated by xenon difluoride. Volume 53. Issue 19. Pages 4582-5. Journal. (1988)

  • ROUTE 4

    • 202112072034374475.jpg

    Reference: Komatsu, Hironori; Umetani, Hideki. Organic Process Research & Development. Synthesis of Trifluorothymidine: Green Glycosylation Condition Using Neither Chloroform nor Transition Metals. Volume 6. Issue 6. Pages 847-850. Journal. (2002)

  • ROUTE 5

    • 202112078594286593.jpg

    Liu, Peng; Liu, Wenbo; Li, Chao-Jun. Catalyst-Free and Redox-Neutral Innate Trifluoromethylation and Alkylation of Aromatics Enabled by Light. Journal of the American Chemical Society. Volume 139. Issue 40. Pages 14315-14321. Journal; Online Computer File. (2017).

  • ROUTE 6

    • 202112073263214761.jpg

    Wang, Limin; Yu, Gaohui; Yao, Feng; Xiong, Jingjing; Tian, He; Han, Jianwei. Preparation method of trifluridine by esterification, halogenation, reduction, trifluoromethylation of hydroxyl group. Assignee Hongene Biotechnology Ltd., Peop. Rep. China; East China University of Science and Technology. CN 107652341. (2018).

  • ROUTE 7

    • 202112071383068171.jpg

    Ji, Yining; Brueckl, Tobias; Baxter, Ryan D.; Fujiwara, Yuta; Seiple, Ian B.; Su, Shun; Blackmond, Donna G.; Baran, Phil S. Innate C-H trifluoromethylation of heterocycles. Proceedings of the National Academy of Sciences of the United States of America. Volume 108. Issue 35. Pages 14411-14415. 2011.

  • ROUTE 8

    • 202112077469302041.jpg

    Fang, Zhongxue; Ning, Yongquan; Mi, Pengbing; Liao, Peiqiu; Bi, Xihe. Catalytic C-H α-Trifluoromethylation of α,β-Unsaturated Carbonyl Compounds. Organic Letters. Volume 16. Issue 5. Pages 1522-1525. 2014

  • ROUTE 9

    • 202112077688431981.jpg

    Kumar, Vineet; Malhotra, Sanjay V. Synthesis of nucleoside-based antiviral drugs in ionic liquids. Bioorganic & Medicinal Chemistry Letters. Volume 18. Issue 20. Pages 5640-5642. 2008.

  • ROUTE 10

    • 202112076504288575.jpg

    Yang, Binghui; Qiu, Jingang; Ling, Guochang. Method for preparation of 5-trifluoromethyl-2'-deoxyuridine. Assignee Hangzhou Fubang Biological Pharmacy Co., Ltd., Peop. Rep. China. CN 1640882 A (2005).

202112071772836102.jpg

Reference: Fernandez-Lucas, Jesus; Fresco-Taboada, Alba; Acebal, Carmen; Mata, Isabel; Arroyo, Miguel. Applied Microbiology and Biotechnology. Enzymatic synthesis of nucleoside analogues using immobilized 2'-deoxyribosyltransferase from Lactobacillus reuteriVolume. 91. Issue 2. Pages 317-327. Journal; Online Computer File (2011)

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Yield:70-00-8 94.3%

Reaction Conditions:

with tert.-butylhydroperoxide in water at -3 - 60; for 2 h;Inert atmosphere;Temperature;

Steps:

2

456 g (2 mol) of 2'-deoxyuridine and 985.2 g (6 mol)95% sodium trifluoromethanesulfinate was added to 7.98 L of purified water, stirred down to -3 ° C, protected by nitrogen stream,After stirring, 772 g (6 mol) of 70% t-butyl hydroperoxide was added dropwise, and the temperature was less than 5 ° C during the dropwise addition,After the dropwise addition, the temperature was raised to 60 ° C, the reaction was stirred for 2 hours, and the reaction was completed.Drop to room temperature, respectively, 8L ethyl acetate extraction 3 times, the combined extract,50 deg.] C and concentrated under reduced pressure to give 558g trifluridine, yield: 94.3%, purity: 97.2%.

References:

CN104761602,2017,B Location in patent:Paragraph 0034; 0035

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