Dimethyl Sulfoxide → tert-butyl N-[(2S)-1-oxo-3-phenylpropan-2-yl]carbamate

Temperature

-78 °C

Oxalyl chloride in anhydrous CH2Cl2 (2.0M, 6.0 mL, 12.0 mmol) was treated with dimethylsulfoxide (1.0 mL, 14.1 mmol) in anhydrous CH2Cl2 (3 mL) dropwise over 5 minutes at −78° C. under a dry N2 atmosphere. The mixture was stirred at −78° C. for 15 minutes and then treated with (2S)-2-(tert-butoxycarbonylamino)-3-phenyl-1-propanol (2.0 g, 8.0 mmol) in anhydrous CH2Cl2 (6 mL) dropwise over 10 minutes. The mixture was stirred at −78° C. for 30 minutes and then treated with triethylamine (4.4 mL, 31.7 mmol) in anhydrous CH2Cl2 (6 mL) dropwise over 10 minutes. The mixture was allowed to slowly warm to ambient temperature, stirred for 1 hour, diluted with CH2Cl2 (100 mL), washed with 10% aqueous citric acid (50 mL), water (50 mL), saturated NaHCO3 (50 mL), dried over Na2SO4, filtered, and the solvent removed under reduced pressure to provide the title compound as an off-white crystalline solid (2.0 g).

1. stirringThe mixture was stirred at −78° C. for 30 minutes
2. temperatureto slowly warm to ambient temperature
3. stirringstirred for 1 hour
4. washwashed with 10% aqueous citric acid (50 mL), water (50 mL), saturated NaHCO3 (50 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. customthe solvent removed under reduced pressure

ORD record

ord-22f341aed6f84948bd99d84a2b8abbbe

Source dataset

uspto-grants-2014_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08741938B2