Nathaniel Kadunce, Olivier St-Jean, Amy Cagulada, Wen-Tau T. Chang, Alexander F. G. Goldberg, Zilin Huang, Jihun Kang, Jinsik Kim, Kyoungchan Kwon, Olga Lapina, Lennie Lin, Trevor J. Rainey, Lyubov Roever, Nisha P. Shah, Scott A. Wolckenhauer
{"title":"Synthetic Development and Scale-Up of a Complex Pyrazole Fragment of Lenacapavir","authors":"Nathaniel Kadunce, Olivier St-Jean, Amy Cagulada, Wen-Tau T. Chang, Alexander F. G. Goldberg, Zilin Huang, Jihun Kang, Jinsik Kim, Kyoungchan Kwon, Olga Lapina, Lennie Lin, Trevor J. Rainey, Lyubov Roever, Nisha P. Shah, Scott A. Wolckenhauer","doi":"10.1021/acs.oprd.4c00235","DOIUrl":null,"url":null,"abstract":"We describe herein the process development and scale-up of a complex cyclopropyl pyrazole fragment of lenacapavir, a drug recently approved for long-acting treatment of HIV (Sunlenca). A ten-step asymmetric synthesis was developed utilizing simple starting materials capable of supporting the commercial supply chain of lenacapavir. Key aspects of this development effort were the oxidation strategy to elaborate the core and optimization of the fluorination reaction to afford the final product.","PeriodicalId":55,"journal":{"name":"Organic Process Research & Development","volume":"27 1","pages":""},"PeriodicalIF":3.1000,"publicationDate":"2024-07-31","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Process Research & Development","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.oprd.4c00235","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
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Abstract
We describe herein the process development and scale-up of a complex cyclopropyl pyrazole fragment of lenacapavir, a drug recently approved for long-acting treatment of HIV (Sunlenca). A ten-step asymmetric synthesis was developed utilizing simple starting materials capable of supporting the commercial supply chain of lenacapavir. Key aspects of this development effort were the oxidation strategy to elaborate the core and optimization of the fluorination reaction to afford the final product.
期刊介绍：
The journal Organic Process Research & Development serves as a communication tool between industrial chemists and chemists working in universities and research institutes. As such, it reports original work from the broad field of industrial process chemistry but also presents academic results that are relevant, or potentially relevant, to industrial applications. Process chemistry is the science that enables the safe, environmentally benign and ultimately economical manufacturing of organic compounds that are required in larger amounts to help address the needs of society. Consequently, the Journal encompasses every aspect of organic chemistry, including all aspects of catalysis, synthetic methodology development and synthetic strategy exploration, but also includes aspects from analytical and solid-state chemistry and chemical engineering, such as work-up tools，process safety, or flow-chemistry. The goal of development and optimization of chemical reactions and processes is their transfer to a larger scale; original work describing such studies and the actual implementation on scale is highly relevant to the journal. However, studies on new developments from either industry, research institutes or academia that have not yet been demonstrated on scale, but where an industrial utility can be expected and where the study has addressed important prerequisites for a scale-up and has given confidence into the reliability and practicality of the chemistry, also serve the mission of OPR&D as a communication tool between the different contributors to the field.
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