Pyridine, hydrofluoride (1:1) → HCID 57305705, compound

Participants

Reaction Steps

To a stirred solution of 17-ethyl-20-fluoro-1-hydroxy-12-[2'-(3"-methoxy-4"-oxocyclohexyl)-1'-methylvinyl]-14-triisopropylsilyloxy-23,25-dimethoxy-13,19,21,27-tetramethyl-11,18-dioxa-4-azatricyclo[22.3.1.04,9 ]-octacos-18-ene-2,3,10, 16-tetraone from Example 23 (870 mg) in tetrahydrofuran (20 ml) contained in a polypropylene vial is added 4 ml of an HF-pyridine solution in tetrahydrofuran and the mixture was stirred at room temperature. The reaction mixture is quenched with sat'd aqueous sodium bicarbonate. The organic layer is separated and the aqueous layer is extracted with ethyl acetate three times. Combined organic layers are washed (sat'd NaHCO3, sat'd NaCl), dried (anhydrous Na2SO4), and filtered. Removal of solvent followed by purification (silica gel column chromatography, gives the title compound.

Provenance & Evidence