Triphenylphosphine → HCID 58691129, compound

Participants

Reaction Steps

Allyl (5R,6S)-3-(3-fluoro-4-methoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (0.807 g), tetrakis(triphenylphosphine)palladium(0) (50 mg) and triphenylphosphine (10 mg) were dissolved in THF (12 mL), and thereto was added at room temperature sodium 2-ethylhexanoate (0.5M ethyl acetate solution, 4.46 mL). The solvent was removed in vacuo, and to the residue was added dichloromethane (10 mL). The mixture was extracted with ion-exchange water (10 mL×3 times) and the aqueous layers were combined and stirred for 1 hour in vacuo. The dichloromethane was removed by distillation and the aqueous layer was purified with C18 reverse column chromatography (Wakosil 40C18, 38φ×60 mm, mobile phase; 0˜5% THF ice-cooled ion-exchange water). The fractions containing the object compound were combined and THF therein was removed in vacuo under stirring for 1 hour. The residue was lyophilized to give sodium (5R,6S)-3-(3-fluoro-4-methoxyphenyl)-6-[(1R)-1-hydroxyethyl]-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (450 mg, yield 59%).

Provenance & Evidence