Tetrabutylammonium Fluoride → tert-Butyl (4-{(2R,3R)-1-(4-chlorophenyl)-3-[(4-methoxybenzyl)thio]-4-oxoazetidin-2-yl}phenoxy)acetate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl (4-{(1R)-1-[(4-chlorophenyl)amino]-2-[(4-methoxybenzyl)thio]-3-oxo-3-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]propyl}phenoxy)acetate (Method 25) (2.3 g, 3.3 mmol) was dissolved in dry toluene (250 mL) and heated to 90° C. under inert atmosphere. N,O-Bis(trimethylsilyl)acetamide (BSA, 2.4 mL, 9.8 mmol) was added and the mixture was stirred at 90° C. for one hour. The mixture was then given 45° C. and tetrabutylammonium fluoride (TBAF, 0.2 g) was added. The mixture was stirred at 45° C. for 2 hours. After cooling, the mixture was concentrated under reduced pressure and purified by flash-chromatography (Heptane:EtOAc 4:1). This afforded the title compound.

Provenance & Evidence