Water → HCID 178435492, compound

Participants

Reaction Steps

To a solution of methyl pheophorbide-a (100 mg, 0.17 mmol) in pyridine (25 mL) was added distilled water (48 μL, 2.7 mmol, 16 equiv.) and the mixture was refluxed under argon with stirring. The reaction was monitored by HPLC (hexane-acetone, 90:10-mobile phase, LiChrospherCN-column, detection at 425 and 410 nm). The HPLC of the reaction aliquots after 2 h and 20 min showed 87% completion (by peak area). After 2 h and 40 min of reflux, more distilled water (32 L, 1.8 mmol, 11 equiv.) was added and reflux continued. An HPLC of reaction aliquot at 5 h and 40 min showed 99.5% completion (by peak area). The solution was cooled to room temperature and solvent removed under reduced pressure. The residue was crystallized from methylene chloride-methanol to give methyl pyropheophorbide-a (50 mg, 56%).

Provenance & Evidence