Dimethyl Sulfoxide → (S)-(1-Methyl-2-oxo-ethyl)-carbamic acid benzyl ester

Dimethylsulfoxide (1.01 g, 918 μL, 12.9 mmol) was added dropwise to a stirred solution of oxalyl chloride (790 mg, 543 μL, 6.23 mmol) in dry CH2Cl2 (12.6 mL) at −78° C. under N2 and the reaction was stirred for 15 min. A solution of benzyl [(1S)-2-hydroxy-1-methylethyl]carbamate (965 mg, 4.61 mmol) in dry CH2Cl2 (12.6 mL) was added dropwise by cannula and the mixture was stirred at −78° C. for 30 min. Triethylamine (1.34 g, 1.85 mL, 13.2 mmol) was added and the reaction was allowed to warm to room temperature and was stirred for 2 h. Water (15 mL) was added and the aqueous phase was separated and extracted with CH2Cl2 (3×15 mL). The combined organic extracts were washed with saturated NaHCO3 and brine, then dried (MgSO4) and concentrated in vacuo to afford benzyl [(1S)-1-methyl-2-oxoethyl]carbamate as a colorless oil. Rf=0.75 (50% EtOAc in hexanes). 1H NMR (500 MHz, CDCl3) δ 9.58 (s, 1H), 7.39-7.35 (m, 5H), 5.39 (br s, 1H), 5.15 (s, 2H), 4.33 (m, 1H), 1.40 (d, J=7.1 Hz, 3H).

1. stirringthe mixture was stirred at −78° C. for 30 min
2. stirringwas stirred for 2 h
3. customthe aqueous phase was separated
4. extractionextracted with CH2Cl2 (3×15 mL)
5. washThe combined organic extracts were washed with saturated NaHCO3 and brine
6. dry with materialdried (MgSO4)
7. concentrationconcentrated in vacuo

ORD record

ord-2eb9865741d545548651436258237e2c

Source dataset

uspto-grants-2010_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07652049B2