Organic Process Research and Development p. 1427 - 1434 (2017)
Update date:2022-08-06
Topics:
Mulder, Jason A.
Gao, Joe
Fandrick, Keith R.
Zeng, Xingzhong
Desrosiers, Jean-Nicolas
Patel, Nitinchandra D.
Li, Zhibin
Rodriguez, Sonia
Lorenz, Jon C.
Wang, Jun
Ma, Shengli
Fandrick, Daniel R.
Grinberg, Nelu
Lee, Heewon
Bosanac, Todd
Takahashi, Hidenori
Chen, Zhidong
Bartolozzi, Alessandra
Nemoto, Peter
Busacca, Carl A.
Song, Jinhua J.
Yee, Nathan K.
Mahaney, Paige E.
Senanayake, Chris H.
A practical and efficient synthesis of the FLAP inhibitor 1 was developed addressing multiple scale-up and safety concerns posed by the established synthesis and utilized a resolution strategy (replacing supercritical fluid chromatography (SFC) separation) for expedient access to the key structural component of 1: the challenging chiral quaternary center. Also highlighted are in situ IR monitoring, condensation to form the 1,2,4-oxadiazole ring, and an efficient Suzuki-Miyaura coupling.
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