Development of a Practical and Scalable Synthesis of the Side Chain for ASP9726, a Successor of Micafungin

Autor:	Norio Hashimoto, Minoru Okada, Yasuhiro Morinaga, Shinya Yoshida, Shigeru Ieda, Atsushi Ohigashi, Takumi Takahashi
Rok vydání:	2013
Předmět:	Successor cardinal Reaction conditions Chemistry business.industry Organic Chemistry Micafungin Nanotechnology Yield (chemistry) Scalability medicine Side chain Physical and Theoretical Chemistry Process engineering business medicine.drug
Zdroj:	Organic Process Research & Development. 17:1252-1260
ISSN:	1520-586X 1083-6160
Popis:	Here, we describe a practical and scalable synthesis of 1, which is a useful side chain of ASP9726 (2), a successor of Micafungin. For large-scale synthesis of 1, reaction conditions were optimized to control impurities and increase yield. In particular, we utilized a high-yield thiadiazole ring formation to prepare thiadiazole 12, a step which was improved by optimization of reaction conditions and isolation method. Further, the number of steps was reduced from 10 to 9, and hazardous reactions were also avoided. Consequently, this process was scaled to produce 21.7 kg of 1 with overall yield improvement from 36.7% to 56.6%.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::94be37a83031f521bccd8a778e8ea708 https://doi.org/10.1021/op400211t Zobrazit plný text záznamu