Triethylamine → (1S)-3-[(2S,3R)-2-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)-1-(4-{3-[(methylsulfonyl)amino]prop-1-yn-1-yl}phenyl)-4-oxoazetidin-3-yl]-1-(4-fluorophenyl)propyl acetate

関与物質

反応手順

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+).

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