Conversion of N4-(α-aminoacyl)cytidines to N-(4-cytidinyl)amino acid amides by a novel rearrangement reaction

ORGN 480

Frantz Victor, f.victor@lilly.com, Deyi Zhang, David M Bender, Jeffrey A Peterson, Robert D Boyer, Gregory A Stephenson, Adam Azman, and James R McCarthy. Lilly Research Laboratories, Eli Lilly and Company, Lilly Corporate Center, Indianapolis, IN 46285
N4-(α-Aminoacyl)cytidines are not stable. Under near neutral or basic conditions the primary N4-(α-aminoacyl)cytidines undergo a facile rearrangement to N-(4-cytidinyl)amino acid amides. The secondary aminoacyl derivatives also undergo the same rearrangement in addition to other competing pathways. This rearrangement is not observed for tertiary aminoacyl derivatives. The structural requirements and implications of this interesting rearrangement will be discussed.
 

New Reactions and Methodology, Heterocycles and Aromatics, Bioorganic Chemistry
8:00 PM-10:00 PM, Tuesday, 12 September 2006 Moscone Center -- Hall D, Poster

Division of Organic Chemistry

The 232nd ACS National Meeting, San Francisco, CA, September 10-14, 2006