Process for the preparation of a ketolide antibiotic

ORGN 814

Timothy B. Towne, tim.towne@abbott.com1, Daniel S. Reno, dreno@endocyte.com1, Deborah A. Davis, Deborah.Davis@abbott.com1, Steven J. Wittenberger, Jianzhang Mei, jianzhang.mei@abbott.com1, Shyamal Parekh1, Marius Naris2, and Eric Kristensen2. (1) GPRD Process Chemistry, Abbott Laboratories, 1401 Sheridan Road, North Chicago, IL 60064, (2) GPRD Analytical Process Research and Development, Abbott Laboratories, 1401 Sheridan Rd, North Chicago, IL 60064
Multi-gram quantities of 1, an Erythromycin A derived ketolide antibiotic, were needed for pre-clinical evaluation. The title compound was prepared in five chemical transformations from the cyclic carbamate 2. Initial route selection and laboratory scale-up will be presented.