Dimethyl Sulfoxide → HCID 18516326, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of oxalyl chloride (0.023 mL, 0.26 mmol) in anhydrous dichloromethane (1 mL) at −78° C. was added DMSO (0.045 mL, 0.63 mmol). After 15 minutes, a solution of Example 237G (0.07 g, 0.21 mmol) in anhydrous 1:4 DMSO/dichloromethane (5 mL) was added dropwise. The reaction was stirred 1 hour at 78° C. then treated with triethylamine (0.15 mL, 1.05 mmol). After 5 minutes, reaction was allowed to warm to room temperature over 1 hour. The reaction was quenched with water (2 mL) and partitioned between EtOAc (50 mL) and sat. aq. NaHCO3 (50 mL). The organic layer was washed with 50% sat. aq. NaHCO3 (2×50 mL), brine (1×50 mL), dried (Na2SO4), filtered, and concentrated. The product was dried in a desiccator to yield the title compound as a white solid (0.07 g, 100%).

Provenance & Evidence