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 (372 mg) in a mixture of tetrahydrofuran (3.2 ml), ethanol (1.6 ml) and water (800 μl) were added triphenylphosphine (17 mg), morpholine (216 μl) and tetrakis(triphenylphosphine)palladium(0) (72 mg) at room temperature for 3 hours under nitrogen atmosphere. The reaction mixture was poured into a mixture of ethyl acetate (40 ml) and water (20 ml). The aqueous layer was separated and concentrated in vacuo to give a residual solution, which was chromatographed on "Diaion HP-20" eluting in turn with water and 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 (20 mg).

Provenance & Evidence