B. Raman, B. Sharma, Rahul R Butala
May 1, 2010
Citations
1
Influential Citations
23
Citations
Journal
Journal of pharmaceutical and biomedical analysis
Abstract
A major process-related impurity associated with the synthesis of ezetimibe was detected by LC-MS. The isolated impurity was found not to have been previously reported. Based on LC/MS/MS studies and accurate mass data, the structure of that impurity was proposed to be 2-(4-hydroxybenzyl)-N,5-bis-(4-fluorophenyl)-5-hydroxypentanamide. The postulated structure was unambiguously confirmed with the help of the NMR and IR analyses of a synthetically obtained sample. The chemical shift of the labile proton of that new entity was assigned by a 2D-NOESY NMR experiment. A rationalization for the formation of this impurity is provided.