Dimethyl Sulfoxide → HCID 18753603, compound

Participants

Reaction Conditions

Reaction Steps

Oxalyl cloride (0.51 g, 4.00 mmol) and dimethyl sulfoxide (0.63 g, 8.01 mmol) were dissolved in dichloromethane (10 ml) and the solution was cooled to −78° C. To the solution, a solution of (±)-1-hydroxymethyl-N-methyl-N-(4-phenoxybenzene-sulfonyl)-2-phthalimidoethylamine (1.70 g, 3.64 mmol), the product of (5) above, in dichloromethane (25 ml) was added dropwise with stirring and this was stirred for 30 minutes. Triethylamine (1.84 g, 18.2 mmol) was added dropwise to the mixture and this was stirred at room temperature for 2 hours. To the reaction mixture, ice-water was added and then this was extracted with dichloromethane. The organic layer was washed with water, dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the desired compound (1.58 g, yield 93%) as a white amorphous solid.

Provenance & Evidence