Dimethyl Sulfoxide → HCID 86600471, compound

Participants

Reaction Steps

A solution of dimethyl sulfoxide (1.6 g, 19 mmol) in dichloromethane (50 mL) was cooled to −78° C. and treated dropwise with oxalyl chloride (1.42 g, 11.2 mmol). After the addition was complete, the solution was stirred for 30 minutes and was then treated dropwise with a solution of [(1R,2S)-2-hydroxymethyl-2-(3-hydroxypropyl)-cyclohexyl]-carbamic acid benzyl ester (0.65 g, 1.9 mmol) in dichloromethane (10 mL). After the addition was complete, the solution was stirred for 40 minutes and then treated with triethylamine (1.8 g, 18 mmol). The mixture was stirred for 30 minutes before removing the cooling bath and stirring at room temperature for 1 hour. The mixture was quenched with saturated aqueous sodium bicarbonate (100 mL) and the organic phase was separated and washed successively with water and saturated aqueous sodium chloride, and then dried over sodium sulfate. The solvent was removed under vacuum to give an oil (0.6 g). 1H NMR (300 MHz, CDCl3) δ9.74 (bs, 1H), 9.43 (bs, 1H), 7.39-7.27 (m, 5H), 5.06 (m, 2H), 4.91 (bd, J=9 Hz, 1H), 4.14 (bm, 1H), 2.60-1.30 (m, 12H). Mass spec (ES+) m/z 318.2 (M+H+, 100%).

Provenance & Evidence