Acetic Anhydride → Erythromycin 2'-acetate

Participants

Reaction Steps

Into a 1.0 L one neck round bottom flask were placed 50 g of erythromycin B (69.64 m mole), 500 mL ethyl acetate and 16 mL acetic anhydride (17.3 g, 169.6 m mole). The solution was stirred at room temperature overnight. Copious amounts of white solids were observed. This mixture was filtered to give 26.2 g solid. The filtrate was washed with 300 mL 5% sodium bicarbonate twice, and the organic layer was dried with magnesium sulfate. The solvent was removed by vacuum distillation to give a second crop of desired product (22.3 g). The product was identified by mass spectroscopy and NMR.

Provenance & Evidence