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

HRID 553480Notes

Reaction equation

HRID 553480 reaction equation
ClCCl.CS(C)=O.C(N(CC)CC)C.[C:15]([O:19][C:20](=[O:26])[N:21]([CH2:23][CH2:24][OH:25])[CH3:22])([CH3:18])([CH3:17])[CH3:16].S(=O)(=O)=O>O>[C:15]([O:19][C:20](=[O:26])[N:21]([CH3:22])[CH2:23][CH:24]=[O:25])([CH3:18])([CH3:17])[CH3:16]

Participants

7

Reactant 5

HCID 679Dimethyl SulfoxideHCID 6344DichloromethaneHCID 8471TriethylamineHCID 24682Sulfur trioxideHCID 545700N-(tert-Butoxycarbonyl)-N-methyl-2-aminoethanol

Product 1

HCID 10725881tert-butyl N-methyl-N-(2-oxoethyl)carbamateYield 62.45%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. temperaturepyridine complex (1.849 moles; 300.3 g), maintaining the reaction temperature less than 20° C
  2. customseparate the organic layer
  3. washwash with 10% citric acid in water (800 mL), water and brine
  4. concentrationConcentrate
  5. washpass through a silica plug, eluting with 20% ethyl acetate/hexanes
  6. concentrationAdd toluene (200 mL) and concentrate

Sources & evidence

ORD record
ord-31a1994e3d99410a8a1d40b4ce91f5bf
Source dataset
uspto-grants-2011_11
Patent number
US08048884B2

Reaction notes

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