title: Synthesis of a potent hNK-1 receptor antagonist via an SN2 reaction of an enantiomerically pure alpha-alkoxy sulfonate.
abstract: The concise synthesis of a stereochemically rich hNK-1 receptor antagonist is described. The synthesis is highlighted by an S(N)2 reaction of an enantiomerically pure alpha-alkoxy sulfonate (orthogonally protected butane triol), which was prepared by utilizing salen-mediated hydrolytic kinetic resolution technology. A stereocontrolled acetalization was employed to connect two enantiomerically pure fragments with a high degree of diastereoselectivity.
authors.affiliation: Department of Process Research, Merck Research Laboratories, 466 Devon Park Drive, Wayne, Pennsylvania 19087, USA. todd_nelson@merck.com
authors.forename: Todd D
authors.initials: TD
authors.lastname: Nelson
authors.forename: Jonathan D
authors.initials: JD
authors.lastname: Rosen
authors.forename: Jacqueline H
authors.initials: JH
authors.lastname: Smitrovich
authors.forename: Joseph
authors.initials: J
authors.lastname: Payack
authors.forename: Bridgette
authors.initials: B
authors.lastname: Craig
authors.forename: Louis
authors.initials: L
authors.lastname: Matty
authors.forename: Mark A
authors.initials: MA
authors.lastname: Huffman
authors.forename: James
authors.initials: J
authors.lastname: McNamara
mesh_terms: D064729:Neurokinin-1 Receptor Antagonists; D013237:Stereoisomerism; D013451:Sulfonic Acids / Q000138:chemical synthesis* / Q000494:pharmacology
chemical_list: D064729:Neurokinin-1 Receptor Antagonists; D013451:Sulfonic Acids