Phosphate → HCID 54369112, compound

Participants

Reaction Steps

A mixture of 4-nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-{(2-ureidoethyl)oxylmethyl}pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.75 g), tetrahydrofuran (40 ml), 0.1M phosphate buffer (pH 6.5) (20 ml) and 20% palladium hydroxide on carbon (0.20 g) was stirred at ambient temperature for 5 hours under atmospheric pressure of hydrogen. The catalyst was removed by filtration and the filtrate was concentrated under reduced pressure to remove tetrahydrofuran. The residual solution was washed with ethyl acetate (40 ml×2) and the organic solvent was removed by evaporation. The residual solution was subjected to a column chromatography on nonionic adsorption resin "Diaion HP-20" (40 ml) eluting with a mixture of acetone and water (5:95 V/V), and lyophilized to give (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-2-{(2-ureidoethyl)oxymethyl}pyrrolidin-4-yl]thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (0.20 g).

Provenance & Evidence