Merck + Co., Inc.

C Scott Shultz

Kevin Campos

Artis Klapars

Robert Wenslow

Lisa F Frey

Yaling Wang

Norihiro Ikemoto

J Michael Williams

J Christopher McWilliams

Cheng-Yi Chen

Andrey V Peresypkin

Alex Minhua Chen

Spencer Dreher

Debra J Wallace

The present invention is directed to a practical process for the preparation of an enamide (II) by palladium catalyzed coupling of a primary amide (IV) with a compound of structural formula (III), as shown below: As well as to crystalline forms of a compound produced by this process, in particular, an anhydrous crystal form, Form B, and crystalline solvates falling into three patterns, Type 1, Type 2, and Type 3, and crystalline intermediate compounds produced in the process. Still further, the present invention relates to the stereoselective reduction of the tetrasubstituted enamide (II) to the corresponding amide (I).

Formation of tetra-substituted enamides and stereoselective reduction thereof

This invention relates to a process for preparing optically active &#x3b1;-amino acid substrates which are used to make potent lethal factor (LF) inhibitors for the treatment of anthrax. This invention further relates to a process for synthesis of potent LF-inhibitors for the treatment of anthrax. Specifically, the invention concerns a novel, high-yielding and highly enantioselective asymmetric hydrogenation reaction of a tetrasubstituted ene-sulfonamide acid or ester.

Process for making N-sulfonated-amino acid derivatives

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Maplewood, NJ, United States of America

C Scott Shultz