Ethanol → 4-Methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid

Participants

Reaction Steps

Tetrakis(triphenylphosphine)palladium(0) [0.32 g) was added to a solution of allyl (4R,5S,6S)-3-[(2S,4S)-1-allyloxycarbonyl-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (2.35 g), morpholine (0.84 ml) and triphenylphosphine (0.24 g) in a mixture of water (3 ml), ethanol (12 ml) and tetrahydrofuran (35 ml) at ambient temperature in a stream of nitrogen, and the mixture was stirred at the same condition for 2 hours to give precipitates. The precipitates were collected by filtration, washed with tetrahydrofuran, and dried over phosphorus pentoxide to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)pyrrolidin-4-yl]thio-6-[(1R)1-hydroxyethyl[-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.67 g).

Provenance & Evidence