Ethanol → FR-27743

Participants

Reaction Steps

To a solution of allyl (4R,5S,6S)-6-[(1R)-1-allyloxycarbonyloxyethyl-3-[(2S,4S)-1-allyloxycarbonyl-2-(2- fluoroethyl)oxymethylpyrrolidin-4-yl]thio-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (350 mg) in a mixture of 4-methyl-2-pentanone (4.2 ml), ethanol (2.1 ml) and water (170 μl) was added triphenylphosphine (16 mg), 5,5-dimethyl-1,3-cyclohexanedione (255 mg) and tetrakis(triphenylphosphine)palladium(0) (68 mg) at room temperature for 3 hours under nitrogen atmosphere. Evaporation of the solvent gave a residue, which was dissolved in a mixture of ethyl acetate (40 ml) and water (20 ml). The aqueous layer was separated and concentrated. The residual solution was chromatographed on "Diaion HP-20" eluting with 10% aqueous acetone. The fractions containing the desired compound were collected, and lyophilized to give (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyl)oxymethylpyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid (100 mg).

Provenance & Evidence