Diastereomeric salt crystallization synthesis for chiral resolution of ibuprofen

Abstract

Conceptual design and experimental investigations are integrated for synthesizing diastereomeric salt crystallization processes for chiral resolution. An anti-inflammatory drug ibuprofen and a common resolving agent N-methyl-D-glucamine were chosen to illustrate this integrative approach. Bench data were generated in a systematic manner. Solvent screening was conducted first to identify the right solvent to precipitate the diastereomeric salts. Solid - liquid equilibrium data of the diastereomeric salt system were then measured. Seeding was used to facilitate the precipitation of the desired component. All of this information was used to generate flow sheet alternatives to recover the desired diastereomeric salts. © 2007 American Institute of Chemical Engineers.