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ChemicalBook CAS DataBase List Bortezomib
179324-69-7

Bortezomib synthesis

5synthesis methods
Bortezomib is a dipeptide boronic acid analogue with antineoplastic activity. Bortezomib reversibly inhibits the 26S proteasome, a large protease complex that degrades ubiquinated proteins. By blocking the targeted proteolysis normally performed by the proteasome, bortezomib disrupts various cell signaling pathways, leading to cell cycle arrest, apoptosis, and inhibition of angiogenesis. Specifically, the agent inhibits nuclear factor (NF)-kappaB, a protein that is constitutively activated in some cancers, thereby interfering with NF-kappaB-mediated cell survival, tumor growth, and angiogenesis. In vivo, bortezomib delays tumor growth and enhances the cytotoxic effects of radiation and chemotherapy.
Synthetic Routes
  • ROUTE 1

    • 202112077992825320.jpg

    Peuchmaur, Marine; Lacour, Marie-Agnes; Sevalle, Jean; Lisowski, Vincent; Touati-Jallabe, Youness; Rodier, Fabien; Martinez, Jean; Checler, Frederic; Hernandez, Jean-Francois. Further characterization of a putative serine protease contributing to the γ-secretase cleavage of β-amyloid precursor protein. Bioorganic & Medicinal Chemistry. Institut des Biomolecules Max Mousseron, UMR5247 CNRS, Faculte de Pharmacie. Universites Montpellier 1 and 2. Montpellier, Fr. 34093. Volume 21. Issue 4. Pages 1018-1029. 2013

  • ROUTE 2

    • 202112079442546855.jpg

    Hinkes, Stefan P. A.; Klein, Christian D. P. Virtues of Volatility: A Facile Transesterification Approach to Boronic Acids. Organic Letters. Institute of Pharmacy and Molecular Biotechnology (IPMB), Medicinal Chemistry. University of Heidelberg. Heidelberg, Germany 69120. Volume 21. Issue 9. Pages 3048-3052. 2019

  • ROUTE 3

    • 202112071841108377.jpg

    Beenen, Melissa A.; An, Chihui; Ellman, Jonathan A. Asymmetric copper-catalyzed synthesis of α-amino boronate esters from N-tert-butanesulfinyl aldimines. Journal of the American Chemical Society. Department of Chemistry. University of California. Berkeley, USA 94720. Volume 130. Issue 22. Pages 6910-6911. 2008

  • ROUTE 4

    • 202112070072387889.jpg

    Zhu, Yongqiang; Zhao, Xin; Zhu, Xinrong; Wu, Gang; Li, Yuejie; Ma, Yuheng; Yuan, Yunxia; Yang, Jie; Hu, Yang; Ai, Li; Gao, Qingzhi. Design, Synthesis, Biological Evaluation, and Structure-Activity Relationship (SAR) Discussion of Dipeptidyl Boronate Proteasome Inhibitors, Part I: Comprehensive Understanding of the SAR of α-Amino Acid Boronates. Journal of Medicinal Chemistry. Jiangsu Simcere Pharmaceutical Research Institute and Jiangsu Key Laboratory of Molecular Targeted Antitumor Drug Research. Nanjing, Peop. Rep. China 210042. Volume 52. Issue 14. Pages 4192-4199. 2009

  • ROUTE 5

    • 202112075483343016.jpg

    Xie, Jian-Bo; Luo, Jian; Winn, Timothy R.; Cordes, David B.; Li, Guigen. Group-assisted purification (GAP) chemistry for the synthesis of Velcade via asymmetric borylation of N-phosphinylimines. Beilstein Journal of Organic Chemistry. Department of Chemistry and Biochemistry. Texas Tech University. Lubbock, USA 79409-1061. Volume 10. Pages 746-751, 6 pp.2014

  • ROUTE 6

    • 202112074732323506.jpg

    Lei, Meng; Zhao, Xin; Wang, Zhanli; Zhu, Yongqiang. Pharmacophore Modeling, Docking Studies, and Synthesis of Novel Dipeptide Proteasome Inhibitors Containing Boron Atoms. Journal of Chemical Information and Modeling. College of Science. Nanjing Forestry University. Nanjing, Peop. Rep. China 210037. Volume 49. Issue 9. Pages 2092-2100. 2009

  • ROUTE 7

    • 202112076071850655.jpg

    Daniels, Blake E.; Stivala, Craig E. A solid-phase approach for the synthesis of α-aminoboronic acid peptides. RSC Advances. Discovery Chemistry. Genentech, Inc.. South San Francisco, USA 94080. Volume 8. Issue 6. Pages 3343-3347. 2018

  • ROUTE 8

    • 202112074111501266.jpg

    Gao, De-Wei; Gao, Yang; Shao, Huiling; Qiao, Tian-Zhang; Wang, Xin; Sanchez, Brittany; Chen, Jason S.; Liu, Peng; Engle, Keary M. Cascade CuH-catalyzed conversion of alkynes to enantioenriched 1,1-disubstituted products. ChemRxiv. Department of Chemistry. The Scripps Research Institute. La Jolla, USA 92037. Pages 1-7. 2019

  • ROUTE 9

    • 202112075068082924.jpg

    Chen, Bo; Huang, Yu. Synthesis of antitumor drug bortezomib. Huaxue Yu Shengwu Gongcheng. Chongqing Taihao Pharmaceutical Co., Ltd. Chongqing, Peop. Rep. China 400039. Volume 31. Issue 6. Pages 42-44. 2014

  • ROUTE 10

    • 202112074503798453.jpg

    Palle, Raghavendracharyulu Venkata; Kadaboina, Rajasekhar; Murki, Veerender; Manda, Amarendhar; Gunda, Nageshwar; Pulla, Ramaseshagiri Rao; Hanmanthu, Mallesha; Mopidevi, Narasimha Naidu; Ramdoss, Suresh Kumar. Preparation of bortezomib in crystalline form. Assignee Dr. Reddy's Laboratories Ltd., India; Dr. Reddy's Laboratories, Inc.WO 2009036281. 2009

202112077992825320.jpg

Peuchmaur, Marine; Lacour, Marie-Agnes; Sevalle, Jean; Lisowski, Vincent; Touati-Jallabe, Youness; Rodier, Fabien; Martinez, Jean; Checler, Frederic; Hernandez, Jean-Francois. Further characterization of a putative serine protease contributing to the γ-secretase cleavage of β-amyloid precursor protein. Bioorganic & Medicinal Chemistry. Institut des Biomolecules Max Mousseron, UMR5247 CNRS, Faculte de Pharmacie. Universites Montpellier 1 and 2. Montpellier, Fr. 34093. Volume 21. Issue 4. Pages 1018-1029. 2013

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Yield:179324-69-7 390 g

Reaction Conditions:

with hydrogenchloride;Dihydroxy-isobutyl-boran in methanol;hexane at 15 - 20; for 1 h;

Steps:

13

Dissolve the spin-dried b8 with methanol (4.75Kg), add it to the 30L reactor, then add n-hexane (3.95Kg) and isobutylboronic acid (0.3Kg), the temperature in the reactor was adjusted to 15-20 ° C, 1N hydrochloric acid (3Kg) was added dropwise, and the addition was completed in about 20-30 minutes. After 1 hour of reaction, the content of b8 was less than 1% by HPLC, and the reaction was terminated. Aspirate the reaction liquid into a 50L liquid separator to separate the n-hexane solution,Add an equal amount of n-hexane for extraction once. Then add pure water (12Kg) and dichloromethane (10Kg) to extract the product, separate the dichloromethane solution, add dichloromethane (5Kg) to extract, combine the extracts, and wash twice with water. Spin dry at 33 ° C, add ethyl acetate (5.52Kg) to dissolve, let stand at room temperature for 2 hours, place in freezer overnight, filter the next day, wash once with ethyl acetate, pump to dry, leave room for 2 hours, vacuum dry at 30 ° C After 10 hours, crude bortezomib (390g) was obtained, the yield in two steps was 67.66%, and the chromatographic purity 99.4%, melting point 169-173 ° C,

References:

CN104860975,2019,B Location in patent:Paragraph 0114; 0116

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