Solid-phase synthesis of isotope-labeled 2-propyloctanoic acid, a therapeutic agent for stroke and Alzheimer's disease

MEDI 290

Jonathan Z. Ho, jonathan_ho@merck.com, Cheng Tang, and Matthew P Braun. Department of Drug Metabolism, Merck & Co., Inc, 126 East Lincoln Avenue, Rahway, NJ 07065

Solid-Phase organic synthesis plays an important role in modern drug discovery.  This technique is widely used as a tool for development of target structure-activity-relationship (SAR) toward lead compounds for drug development.  However, utilization of solid-phase synthesis in obtaining small molecule isotopically labeled compounds has only been scarcely explored.  Hence, we sought to develop an efficient solid-phase synthetic strategy that would allow the preparation of carboxylic acids, particularly, those for which standard purification and isolation would be difficult due to lack of a UV chromophore.  We report herein a convenient method that takes advantage of the oxime resin as a solid support.  Two C-isotope labeled compounds were made by application of this technology.

 

 

 

Poster Session
7:00 PM-9:00 PM, Wednesday, August 22, 2007 BCEC -- Exhibit Hall - B2, Poster

Division of Medicinal Chemistry

The 234th ACS National Meeting, Boston, MA, August 19-23, 2007