Erythromycin → Flurithromycin

Participants

Reaction Steps

Erythromycin A (3 g, 4.1 mmole) was dissolved in glacial acetic acid (12 mL) at room temperature and stirred for 2 hours. N-fluorobenzenesulfonimide (1.6 g, 4.1 mmole) was added and stirring continued for an additional 4 hours at 22° C. The reaction was worked-up in the same manner as Example 1 to afford 2.533 g of crude flurithromycin. This material was recrystallized as described in Example 1 to yield 0.8 g (26% yield) of flurithromycin. This example shows the embodiment of the invention where the anydro derivative of erythromycin is prepared as an unisolated reaction intermediate and the N-F fluorination reaction is carried out without a buffer.

Provenance & Evidence