Lab-Scale Preparation of a Novel Carbocyclic Chemokine Receptor Antagonist
| العنوان: | Lab-Scale Preparation of a Novel Carbocyclic Chemokine Receptor Antagonist |
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| المؤلفون: | Shawn Branum, Fawzy Nagy E, Christopher A. Teleha, Luc Van Der Steen, Mark J. Wall, Derek A. Beauchamp, Michael Reuman, Marc Verbeek, Michael Kolpak, Zhihua Sui, Chaozhong Cai, Gregory C. Leo, Ronald K. Russell, Yongzheng Zhang, Fu-An Kang, Hilde Vanbaelen |
| المصدر: | Organic Process Research & Development. 18:1622-1629 |
| بيانات النشر: | American Chemical Society (ACS), 2014. |
| سنة النشر: | 2014 |
| مصطلحات موضوعية: | chemistry.chemical_classification, Chemokine Receptor Antagonist, Chemokine receptor, chemistry, Bicyclic molecule, Stereochemistry, Carboxylic acid, Organic Chemistry, Diastereomer, Physical and Theoretical Chemistry, Radical cyclization, Reductive amination, Coupling reaction |
| الوصف: | The preparation of a novel chemokine receptor type 2 (CCR-2) antagonist is described on a 135 g scale. The synthesis of an all-carbon bicyclic core was accomplished using a radical cyclization strategy using chiral precursors, wherein elaboration led to N-Boc carboxylic acid in good yield. After amidation using a traditional coupling reaction, a reductive amination using enantiomerically enriched 3-methoxy-4-pyranone led to the final compound. Although several steps of the syntheses involved reagents that would not be preferred in process and chromatography was used to provide the free-base diastereomer of the final succinate salt, the overall route went through stable intermediates that could be used for future scale-up. This lab-scale synthesis struck a balance between a quick scale-up and a more thorough process review of all possible methods and routes. |
| تدمد: | 1520-586X 1083-6160 |
| DOI: | 10.1021/op500265z |
| URL الوصول: | https://explore.openaire.eu/search/publication?articleId=doi_________::30ed40727f516d73f0e1e4e53e8301d9 https://doi.org/10.1021/op500265z |
| رقم الانضمام: | edsair.doi...........30ed40727f516d73f0e1e4e53e8301d9 |
| قاعدة البيانات: | OpenAIRE |
| تدمد: | 1520586X 10836160 |
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| DOI: | 10.1021/op500265z |