Acetic Acid → HCID 86744492, compound

Participants

Reaction Steps

To a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-chloroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-(t-butyldimethylsilyloxy)ethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.72 g) in tetrahydrofuran (7.2 ml) were added glacial acetic acid (0.65 ml) and a 1M solution (5.6 ml) of tetrabutylammonium fluoride in tetrahydrofuran in a stream of nitrogen, and the mixture was stirred at room temperature for 10 hours. To the mixture was added ethyl acetate (50 ml). The solution was washed with water (50 ml×3), dried over magnesium sulfate and concentrated under reduced pressure to give a syrup. The syrup was chromatographed on silica gel (10 g) and eluted with a mixture of hexane and ethyl acetate (80:20 V/V) to give allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-chloroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.30 g).

Provenance & Evidence