Dimethyl Sulfoxide → tert-butyl N-(2-oxoethyl)carbamate

To a solution of 700 mg (4.34 mmol) of 2-(t-butoxycarbonylamino)ethanol in 35 mL of dry methylene chloride was added 4.0 mL of dimethylsulfoxide and 4.8 mL (35 mmol) of triethylamine, followed by 2.8 g (17 mmol) of pyridine sulfur trioxide complex in three portions over 5 minutes. The reaction was stirred at room temperature for 3 hours then diluted with 500 mL of ether. The mixture was transferred to a separatory funnel and washed with 1N HCl (2×50 ml), saturated aqueous sodium bicarbonate (100 mL), and brine (100 mL). The organic layer was dried over magnesium sulfate, filtered, and the solvent removed under vacuum to afford 550 mg (80%) of product which was used without further purification. 1H NMR (200 MHz,CDCl3): 1.40 (s,9H), 4.05 (d,7 Hz,2H), 5.17 (s,1H), 9.62 (s,1H).

1. customThe mixture was transferred to a separatory funnel
2. washwashed with 1N HCl (2×50 ml), saturated aqueous sodium bicarbonate (100 mL), and brine (100 mL)
3. dry with materialThe organic layer was dried over magnesium sulfate
4. filtrationfiltered
5. customthe solvent removed under vacuum

ORD record

ord-7d09254376464ed9a331c978794960a7

Source dataset

uspto-grants-1994_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05310737