Dimethyl Sulfoxide → HCID 18419520, compound

Participants

Reaction Steps

To a solution of DMSO (0.31 mL, 3.54 mmole) in CH2Cl2 (5 mL) at −78° C. was added oxalyl chloride (0.13 mL, 1.77 mmole) dropwise. After 10 min, a solution of 2-[N-(3-hydroxy-1-butyl)-N-(tert-butoxycarbonyl)amino]pyridine-N-oxide (500 mg, 1.77 mmole) in CH2Cl2 (5 mL) was added dropwise. After 30 min, Et3N (0.81 mL, 5.84 mmole) was added, and the mixture was warmed gradually to RT. After 20 min, the mixture was diluted with CH2Cl2 (20 mL) and washed sequentially with 10 mL each H2O, 10% HCl, H2O, and brine. The organic layer was dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound (455 mg, 92%) as a colorless oil. This was used without purification: MS. (ES) m/e 281 (M+H)+.

Provenance & Evidence