Dimethyl Sulfoxide → HCID 86754800, compound

Participants

Reaction Steps

To a solution of 5.9 g (7.4 mmol) of 2'-O-Acetyl-9-deoxo-8a-aza-8a-methyl-8a-homoerythromycin A in 100 ml of dry methylene chloride under nitrogen at room temperature was successively added 5.3 ml (74.7 mmol) of dimethyl sulfoxide, 7.15 g (19.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 7.15 g (37 mmol) of pyridinium trifluoroacetate. The reaction mixture was stirred for 2 hours, at which point 300 ml of ethyl acetate followed by 100 ml of water was added. The pH of the solution was adjusted to the range of 9-10 with 1N sodium hydroxide solution. The ethyl acetate layer was washed with brine, dried (anhydrous sodium sulfate) and evaporated. Silica chromatography with ethyl acetate-acetone-ammonium hydroxide (9:1:0.1) gave 4.8 g (82% yield) of the title compound as a white solid.

Provenance & Evidence