Dimethyl Sulfoxide → tert-butyl N-methyl-N-(2-oxoethyl)carbamate

Participants

Reaction Steps

Combine under a nitrogen atmosphere, dichloromethane (37.91 moles; 2.43 L), dimethyl sulfoxide (7.30 moles; 518.4 mL), triethylamine (1.85 moles; 257.7 mL), and (2-hydroxy-ethyl)-methyl-carbamic acid t-butyl ester (924.5 mmoles; 162.0 g). Add in steps sulfur trioxide:pyridine complex (1.849 moles; 300.3 g), maintaining the reaction temperature less than 20° C. Stir the reaction mixture at ambient temperature overnight. Add 1.0 L water, separate the organic layer, wash with 10% citric acid in water (800 mL), water and brine. Concentrate and pass through a silica plug, eluting with 20% ethyl acetate/hexanes. Add toluene (200 mL) and concentrate to provide the title intermediate (yield 62.45%, 100 g).

Provenance & Evidence