Dimethyl Sulfoxide → Benzyl 2-oxopropylcarbamate

Temperature

-78 °C

To a solution of oxalyl chloride (37 mL, 2 M solution in CH2Cl2, 74 mmol) in CH2Cl2 (60 mL) at −78° C. under argon was added DMSO (7.8 g, 100 mmol). The mixture was stirred at −78° C. for 20 min, and to this mixture was added a solution of 1-benzyloxycarbonylamino-2-propanol (2) (12.9 g, 61.8 mmol) in CH2Cl2 (40 mL). The mixture was stirred at −78° C. for 1 h, and then Et3N (21 mL) was added to the mixture. The mixture was warmed to room temperature and washed with 1 N hydrochloric acid followed by aqueous sodium bicarbonate solution. The organic solution was dried over Mg2SO4 and concentrated to afford 1-benzyloxycarbonylamino-2-propanone (10.2 g, 81%) as a solid, which was used without further purification in the next step. 1H NMR (CDCl3): □ 7.32 (m, 5H), 5.50 (s, 1H), 5.06 (s, 2H), 4.07 (s, 2H), 2.1 (s, 3H)

1. stirringThe mixture was stirred at −78° C. for 1 h
2. temperatureThe mixture was warmed to room temperature
3. washwashed with 1 N hydrochloric acid
4. dry with materialThe organic solution was dried over Mg2SO4
5. concentrationconcentrated

ORD record

ord-94190286fc6e4421925b30e93ae48177

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07511063B2