Water → HCID 178435492, compound

Participants

Reaction Steps

Methyl pheophorbide-a (23 g, 37.9 mmol) was added to distilled 2,4,6-collidine (700 mL, Aldrich) and the mixture was refluxed under argon with stirring. After 7 hours of reflux, TLC showed the majority of methyl pheophorbide-a remained. Distilled water (2.5 mL, 139 mmol, 3.7 equiv.) was added and the solution was continued to reflux under argon. After 45 min. the reaction was complete by TLC. The solution was cooled to room temperature and solvent removed under reduced pressure. The residue was precipitated from methylene chloride/methanol, then purified on a silica gel column. The desired fraction was collected, solvent was evaporated off, and the fraction was precipitated from methylene chloride/methanol to give methyl pyropheophorbide-a (17 g, 81%).

Provenance & Evidence