反应详情

温度

50 °C

Methyl {4-[(2R,3R)-3-{[(2R)-2-{[tert-butyl(dimethyl)silyl]oxy}-2-(4-fluorophenyl)ethyl]thio}-1-(4-iodophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate (500 mg, 0.69 mmol) and N-prop-2-yn-1-ylmethanesulfonamide (150 mg, 1.13 mmol) were mixed in 15 ml water and 4 ml MeCN. K2CO3 (220 mg, 1.59 mmol), Pd(PPh3)4 (40 mg, 5 mol %) and CuI (13 mg, 10 mol %) were added. The solution was stirred at 50° C. for 2 h and at ambient temperature over night. EtOAc (20 ml) and 2 M HCl (1 ml) were added. The mixture was stirred for 5 min and the phases were separated. The aqueous phase was extracted with EtOAc. The combined organic phases were washed with 2% NaHCO3, brine (2×), dried with MgSO4 and concentrated to yield the title compound. M/z: 725.3 (M−1). 1H-NMR (400 MHz, DMSO-d6) δ: −0.18 (s, 3H), −0.04 (s, 3H), 0.77 (s, 9H), 2.85-3.02 (m, 5H), 3.69 (s, 3H), 3.80 (dd, 1H), 4.01 (d, 2H), 4.29 (d, 1H), 4.79 (s, 2H), 4.91 (dd, 1H), 5.11 (d, 1H), 6.95 (d, 2H), 7.09-7.18 (m, 2H), 7.18-7.25 (d, 2H), 7.32-7.42 (m, 6H).

1. stirringThe mixture was stirred for 5 min
2. customthe phases were separated
3. extractionThe aqueous phase was extracted with EtOAc
4. washThe combined organic phases were washed with 2% NaHCO3, brine (2×)
5. dry with materialdried with MgSO4
6. concentrationconcentrated