反应详情

A solution of 0.5 g (0.742 mmol, 1 equiv) (1S)-3-[(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-(4-iodophenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate (intermediate of step A), 0.198 g (1.48 mmol, 2 equiv.) N-prop-2-yn-1-ylmethanesulfonamide (i-5), 0.086 g (0.074 mmol, 0.1 equiv.) tetrakistriphenylphosphine palladium(0) and 7 mg (0.04 mmol, 0.05 equiv) copper(I) iodide in 8 mL methylene chloride was deoxygenated by a slow stream of anhydrous nitrogen delivered by a needle through a rubber septum. To the resulting solution was added by syringe 1 mL (7.42 mmol, 10 equiv.) triethylamine. The resulting solution was stirred at room temperature for 4.5 hr at which time the mixture was partitioned 5 mL of a 5% aq. solution of citric acid. The mixture was transferred to a spearatory funnel and extracted with EtOAc (3×5 mL) and methylene chloride (2×5 mL) The combined organic extracts were dried over anhydrous Na2SO4 filtered and the solvent removed under vacuum. The residue was purified by prep. Tlc eluting with EtOAc/hexanes (4/1) followed by further purification by prep. Tlc eluting with EtOAc/hexanes (1/1) to afford the title compound. m/z (ES) 619.0 (M−HOAc+).

1. customwas partitioned 5 mL of a 5% aq. solution of citric acid
2. customThe mixture was transferred to a spearatory funnel
3. extractionextracted with EtOAc (3×5 mL) and methylene chloride (2×5 mL) The combined organic extracts
4. dry with materialwere dried over anhydrous Na2SO4
5. filtrationfiltered
6. customthe solvent removed under vacuum
7. customThe residue was purified by prep
8. customTlc eluting with EtOAc/hexanes (4/1) followed by further purification by prep