Ethyl Acetate → HCID 58691124, compound

Participants

Reaction Steps

Allyl (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(3-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (1.37 g, 3.99 mmol) prepared by Reference Example 3, triphenylphosphine (52 mg), and tetrakis(triphenylphosphine)palladium(0) (0.23 g, 0.2 mmol) were dissolved in THF (20 ml), and thereto was added at 0° C. sodium 2-ethylhexanoate in ethyl acetate (0.5 M, 8.0 ml, 4.0 mmol), followed by stirring for 1 hour. Thereto was added hexane (30 ml) and the resulting white crystals were filtered under a nitrogen atmosphere, washed with hexane, dried at room temperature in vacuo to give a crude product. The product was dissolved in a small amount of ice-water, and purified with C18 reverse column chromatography (filler: Akosil 40C18 (Wako Pure Chemical Ind.); mobile phase; 0˜5%THF/ice-cooled ion-exchange water). The fractions containing the object compound were combined and THF therein was removed at room temperature in vacuo under stirring for 1 hour. The residue was lyophilized to give sodium (5R,6S)-6-[(1R)-1-hydroxyethyl]-3-(3-methoxyphenyl)-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate (297 mg, yield 23%).

Provenance & Evidence