N,O-bis(trimethylsilyl)acetamide → tert-Butyl {4-[(2R,3R)-3-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-1-(4-fluorophenyl)-4-oxoazetidin-2-yl]phenoxy}acetate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (4-{(1R,2R)-2-({[2-(1,3-benzodioxol-5-yl)-5,5-dimethyl-1,3-dioxan-2-yl]methyl}thio)-1-[(4-fluorophenyl)amino]-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate (Method 15) (22.30 g, 27.4 mmol) was dissolved in dry toluene (800 mL) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 20.1 mL, 82.1 mmol) was added and the mixture was stirred at 90° C. for one hour. The mixture was then given 45° C. and tetrabutylammonium fluoride trihydrate (TBAF, cat., 1 g) was added and the mixture was stirred at 45° C. for 1 hour. The mixture was then concentrated under reduced pressure and purified by flash-chromatography (heptane:EtOAc 5:1). This afforded 10.0 g (56%) of the title compound as a white solid.

Provenance & Evidence