Hydrochloric Acid → (3S,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone

Participants

Reaction Steps

Trimethylsilyl trifluoromethanesulfonate (0.48 ml) was added to a mixture of (3R,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone (0.15 g), triethylamine (0.4 ml) and dichloromethane (7 ml) at 5° C. The mixture was stirred at ambient temperature for 3 hours and poured into a mixture of ethyl acetate (70 ml), ethanol (10 ml), 10% hydrochloric acid (10 ml) and water (50 ml). After stirring for 30 min. at ambient temp., the organic layer was separated, washed successively with brine, saturated aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated under reduced pressure. The precipitates were recrystallized from n-hexane to give 0.13 g of (3S,4S)-3-[(R)-1-hydroxyethyl]-4-trimethylsilylethynyl-2-azetidinone.

Provenance & Evidence