Convenient synthesis and isolation of ACC and N-protected ACC derivatives

ORGN 644

Shawn P. Allwein1, Elizabeth A. Secord1, Andrew Martins2, Jeffrey V. Mitten1, Todd D. Nelson1, Michael H. Kress1, and U H. Dolling1. (1) Department of Process Research, Merck Research Laboratories, 466 Devon Park Drive, WYN-3, Wayne, PA 19087, (2) University of Toronto
1-Aminocyclopropane-1-carboxylic acid (ACC) and its derivatives have been identified as key subunits contained in biologically active natural products and pharmaceutical agents. A convenient synthesis to ACC and N-protected derivatives was developed. This route utilizes a bisalkylation of a N-benzyl glycine derived imine followed by global deprotection via hydrogenation. Direct isolation of ACC from a non-aqueous stream or immediate conversion to N-protected derivatives in a single flask will be described.

 

New Reactions, Methodology, Heterocycles, Aromatics
8:00 PM-10:00 PM, Wednesday, August 25, 2004 Pennsylvania Convention Center -- Hall D, Poster

Division of Organic Chemistry

The 228th ACS National Meeting, in Philadelphia, PA, August 22-26, 2004