Dimethyl Sulfoxide → HCID 131733852, compound

Participants

Reaction Steps

To a solution of (S)-tert-butyl (1-((tert-butyldiphenylsilyl)oxy)-4-hydroxybutan-2-yl)carbamate (prepared according to the procedure described in WO2013124826 A1 using L-aspartic acid) (15.0 g, 33.8 mmol) and DIPEA (29.5 mL, 169 mmol) in DCM (50 mL) at 0° C. was added a slurry of DMSO (7.20 mL, 101 mmol) and sulfurtrioxide pyridine complex (16.14 g, 101 mmol) in DCM (50 mL). After stirring at rt for 1.5 h, the mixture was diluted with saturated NaHCO3 (aq) and the layers were separated. The aqueous layer was extracted with DCM and the combined organic portions were dried over Na2SO4 and concentrated in vacuo to afford the title compound (16.9 g, assumed quantitative) as a ight brown oil. It was used as such without further purification. LCMS: Rt=1.20 min, m/z=442.2 (M+1) Method 2m_acidic.

Provenance & Evidence