Erythromycin → Flurithromycin

Participants

Reaction Steps

Erythromycin A (5 g, 6.813 mmole) and N-fluorobenzenesulfonimide (2.2 g 6,813 mmole) were dissolved in glacial acetic acid (20 mL) at room temperature and stirred for 18 hours. The reaction was worked-up in the same manner as Example 1 to afford 4.96 g of crude flurithromycin. This material was recrystallized as described in Example 1 to yield 2.25 g (44% yield) of fluorithromycin. This example shows that reasonably good yields of flurithromycin may be obtained in the process of the invention without buffering.

Provenance & Evidence