Dimethyl Sulfoxide → Benzyl N-methyl-N-(2-oxoethyl)carbamate

HRID 2109677Notes

Reaction equation

HRID 2109677 reaction equation
CS(C)=O.CCN(C(C)C)C(C)C.[CH2:14]([O:21][C:22]([N:24]([CH2:26][CH2:27][OH:28])[CH3:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl>[CH2:14]([O:21][C:22]([N:24]([CH2:26][CH:27]=[O:28])[CH3:25])=[O:23])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 13279869N-Cbz-N-methyl-2-aminoethanol

Product 1

HCID 12010768Benzyl N-methyl-N-(2-oxoethyl)carbamateYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-10 °C

Procedure

DMSO (71 mL, 1 mol) and DIPEA (87.1 mL, 0.5 mol) were added to a stirred solution of the product of step (a) (20.9 g, 0.1 mol) in dichloromethane (200 mL) at −10° C. The reaction mixture was stirred at −10° C. for 15 min and then sulfur trioxide pyridine complex (79.6 g, 0.5 mol) was added and the resulting mixture was stirred for 1 hour. The reaction mixture was quenched with addition of 1 M hydrochloric acid (200 mL). The organic layer was separated and washed with saturated aqueous sodium bicarbonate (100mL), brine (100 mL), dried (potassium carbonate) and solvent removed under reduced pressure to give the title compound (20.7 g, ˜100% yield).

Workup

  1. additionsulfur trioxide pyridine complex (79.6 g, 0.5 mol) was added
  2. stirringthe resulting mixture was stirred for 1 hour
  3. customThe reaction mixture was quenched with addition of 1 M hydrochloric acid (200 mL)
  4. customThe organic layer was separated
  5. washwashed with saturated aqueous sodium bicarbonate (100mL), brine (100 mL)
  6. dry with materialdried (potassium carbonate) and solvent
  7. customremoved under reduced pressure

Sources & evidence

ORD record
ord-e9479ec0a564461b85aed86ab982c2c8
Source dataset
uspto-grants-2009_04
Patent number
US07514558B2

Reaction notes

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