Dimethyl Sulfoxide → benzyl N-(2-oxoethyl)carbamate

A solution (30 ml) of oxalyl chloride (1.72 ml, 20.0 mmol) in dichloromethane was added dropwise to a solution (10 ml) of dimethyl sulfoxide (2.84 ml, 40.0 mmol) in dichloromethane at −78° C., and the mixture was stirred at the same temperature for 5 min. A solution (45 ml) of benzyl(2-hydroxyethyl)carbamate (1.95 g, 10.0 mmol) in dichloromethane was added to the reaction mixture and the mixture was further stirred for 15 min. Triethylamine (6.93 ml, 50.0 mmol) was added, and the mixture was stirred for 5 min. The temperature was raised to room temperature and the reaction mixture was stirred for 1.5 hrs. The reaction mixture was concentrated under reduced pressure, water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous MgSO4, and concentrated under reduced pressure. The obtained residue was subjected to silica gel column chromatography and eluted with hexane-ethyl acetate (7:3-3:2, v/v) to give the title compound (930 mg, 48%) as a colorless oil. 1H-NMR (CDCl3) δ: 4.14 (2H, d, J=5.1 Hz), 5.13 (2H, s), 5.47 (1H, br), 7.31-7.37 (5H, m), 9.64 (1H, s).

1. stirringthe mixture was further stirred for 15 min
2. stirringthe mixture was stirred for 5 min
3. stirringthe reaction mixture was stirred for 1.5 hrs
4. concentrationThe reaction mixture was concentrated under reduced pressure, water
5. additionwas added to the residue
6. extractionthe mixture was extracted with ethyl acetate
7. washThe extract was washed with saturated brine
8. dry with materialdried over anhydrous MgSO4
9. concentrationconcentrated under reduced pressure
10. washeluted with hexane-ethyl acetate (7:3-3:2

ORD record

ord-c3e5970390b64424a62dee9347b8fdef

Source dataset

uspto-grants-2011_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07943770B2