Potassium Phosphate, Dibasic → Benzyl ((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Participants

Reaction Conditions

Reaction Steps

To a solution of benzyl ((2R,3S)-2-((4-(1-((tert-butyldiphenylsilyl)oxy)ethyl)-2H-1,2,3-triazol-2-yl)methyl)-1-(2,4-dimethoxybenzyl)-4-oxoazetidin-3-yl)carbamate (2.50 g, 3.41 mmol) in ACN/water (2:1, 45 mL) at room temperature was added K2S2O8 (1.57 mg, 5.79 mmol) and K2HPO4 (949 mg, 5.45 mmol). The mixture was heated to 90° C. under nitrogen with stirring for 6 h. The reaction mixture was concentrated in vacuo to remove ACN. To the resulting slurry was added EtOAc and water. The organic layer was separated and the aqueous layer was extracted with EtOAc (2×). The organic portions were combined, dried with Na2SO4, filtered and concentrated in vacuo. Purification of the crude residue via silica gel chromatography (EtOAc-Heptane, 30-60%) afforded the title compound (1.35 g, 68%). LCMS: Rt=1.18 min, m/z=584.3 (M+1) Method 2m_acidic.

Provenance & Evidence