Acetic Anhydride → 5-Acetylaminomethyl-2-oxazolidinone

Participants

Reaction Steps

A solution of 1.42 g (3.38 mmol) of the azide 11 in 200 mL ethyl acetate was treated with 400 mg of 10% Palladium on carbon followed by hydrogenation at atmospheric pressure for 48 hours. The resulting ethyl acetate solution of 12 was treated with 1.34 g (1.37 mL, 16.9 mmol) of pyridine and 870 mg (0.80 mL, 8.5 mmol) of acetic anhydride followed by stirring at ambient temperature for 48 hours. The solution was treated with 1.37 mL pyridine and 0.8 mL acetic anhydride followed by stirring at ambient temperature for another 48 hours. The solution was filtered through celite, washing the filter cake with ethyl acetate. The filtrate was washed with water (4×50mL), 1.0M CuSO4 solution (50 mL), and again with water (50 mL). Drying (Na2SO4) and concentration in vacuo afforded a foam which was diluted with dichloromethane and stirred for 1 hour with saturated NaHCO3 solution. The mixture was extracted with dichloromethane and the combined organic layers were dried (Na2SO4) and concentrated in vacuo to afford an amber oil which was chromatographed over 74 g of 230-400 mesh silica gel, eluting with 2% (v/v) methanol in dichloromethane and then with 5% (v/v) methanol in dichloromethane. These procedures afforded 1.19 g (81%) of 3-(3-fluoro-4-tert-butoxycarbonylpiperazin-1-yl)phenyl)-5-acetylaminomethyl-2-oxazolidinone (21) as a rigid off-white foam, mp=162°-164° C.

Provenance & Evidence