Phosphate → FR-27743

Participants

Reaction Steps

To a solution of allyl (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)-pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (4.00 g), sodium 2-ethylhexanoate (1.21 g), and triphenylphosphine (0.35 g) in tetrahydrofuran (120 ml) was added tetrakis(triphenylphosphine)palladium(0) (0.77 g) at ambient temperature in a stream of nitrogen. The mixture was stirred at the same condition for one hour. To the mixture was added 0.1M phosphate buffer (pH 6.0) (120 ml). The mixture was stirred in the presence of 20% palladium hydroxide on carbon (0.8 g) under atmospheric pressure of hydrogen at ambient temperature for 4 hours. The catalyst was filtered off and the filtrate was concentrated under reduced pressure to remove the tetrahydrofuran. An aqueous solution was washed with ethyl acetate (100 ml×3) and the organic solvent was removed by evaporation. The residual solution was subjected to a column chromatography on nonionic adsorption resin, "Diaion HP-20" (100 ml) and eluted with a mixture of acetone and water (7:93 V/V). The fractions containing the desired compound were collected and lyophilized 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 as a solid (1.36 g). ##STR31##

Provenance & Evidence