Synthesis of an influenza neuraminidase inhibitor intermediate via a highly diastereoselective coupling reaction.
[reaction: see text]. A highly diastereoselective coupling reaction between TBSOP (3) and trityl sulfenimine 4 was developed which provided influenza neuraminidase inhibitor intermediate 7 in 80% yield and >99% de after crystallization. The reaction was shown to be reversible with the high diastereoselectivity resulting from a favorable H-bonding interaction in the major diastereomer.
Barnes
David M
DM
Global Pharmaceutical R&D, Process Research & Development, Abbott Laboratories, 1401 Sheridan Road, D-R450, Bldg. R8, North Chicago, Illinois 60064-4000, USA.
McLaughlin
Maureen A
MA
Oie
Tetsuro
T
Rasmussen
Michael W
MW
Stewart
Kent D
KD
Wittenberger
Steven J
SJ
D002851:Chromatography, High Pressure Liquid; D003460:Crystallization; D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000494:pharmacology*; D006860:Hydrogen Bonding; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D009439:Neuraminidase / Q000037:antagonists & inhibitors*; D009975:Orthomyxoviridae / Q000201:enzymology*; D011759:Pyrrolidines / Q000138:chemical synthesis* / Q000494:pharmacology*; D013237:Stereoisomerism
C456059:A 315675; D004791:Enzyme Inhibitors; D007202:Indicators and Reagents; D011759:Pyrrolidines; D009439:Neuraminidase