Tetrabutylammonium Fluoride → Benzyl((2R,3S)-2-((4-(hydroxymethyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate

Participants

Reaction Steps

To a solution of benzyl ((2R,3S)-2-((4-(((tert-butyldimethylsilyl)oxy)methyl)-2H-1,2,3-triazol-2-yl)methyl)-4-oxoazetidin-3-yl)carbamate (10.8 g, 24.4 mmol) in THF (100 mL) was added TBAF (1 M in THF, 26.6 mL, 26.6 mmol) slowly over a period of 15 min. After stirring at rt for 1.5 h, the reaction mixture was concentrated in vacuo. The crude residue was purified via silica gel chromatography (MeOH-DCM, 1-5%) to afford the title compound (6.8 g, 85%) as a pale yellow solid. LCMS: m/z=330.0 (M+1).

Provenance & Evidence