Ammonia → N-Demethylerythromycin A

Participants

Reaction Steps

5 g of erythromycin A and 4.7 g of sodium acetate (×3 H2O) were dissolved in 200 ml of an 8:2 methanol/water mixture. 1.75 g of iodine were added to the solution, and the reaction mixture was then irradiated with a quartz lamp at room temperature for 20 minutes. Subsequently, half the solvent was evaporated, and the remaining reaction mixture was poured into a mixture of 140 ml of water and 10 ml of ammonia. The reaction mixture was extracted three times with 20 ml portions of methyl t-butyl ether. The ether extract was separated and some of the ether was evaporated. The reaction product was then left to crystallize out and was recrystallized from acetone. 2 g of N-demethylerythromycin A were obtained.

Provenance & Evidence