Water → HCID 22476611, compound

Participants

Reaction Conditions

Reaction Steps

Into a flame dried 250 mL 3 neck flask fitted with a thermometer and magnetic stirrer, DMSO (2.61 mL) in methylene chloride (10 mL) was added dropwise to oxalyl chloride (1.60 mL) in methylene chloride (50 mL) while stirring at −55° C. under a nitrogen atmosphere. After 2 minutes, (2-hydroxycyclohexyl)[(methylethyl)sulfonyl]amine (3.60 g, 16.3 mmol) in methylene chloride (10 mL) was added dropwise at this temperature and the reaction was stirred for an additional 15 minutes. Triethylamine (10.8 mL) was then added dropwise and the reaction was allowed to warm to room temperature. Water (76 mL) was added at room temperature and the layers were separated. The organic layer was washed once with water, dried over potassium carbonate filtered, and concentrated under reduced vacuum to yield 3.90 g as an orange solid. This material was purified via silica gel chromatography employing the Water's Prep. 2000 and eluting with a solvent of methylene chloride/ethyl acetate 19:1 to yield the intermediate title compound (2.94 g, 82%) as a white solid. FD M.S. 219.2 (M*). Calculated for C9H17NO3S: Theory: C 49.29, H 7.81, N 6.39. Found: C 49.18, H 7.84, N 6.39.

Provenance & Evidence