Dimethyl Sulfoxide → Acetic acid [benzyl-(2-oxo-ethyl)carbamoyl]methyl ester

HRID 1423293Notes

Reaction equation

HRID 1423293 reaction equation
[CH2:1]([N:8]([CH2:16][CH2:17][OH:18])[C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CS(C)=O.C(N(CC)C(C)C)(C)C>C(OCC)(=O)C>[CH2:1]([N:8]([CH2:16][CH:17]=[O:18])[C:9]([CH2:11][O:12][C:13](=[O:15])[CH3:14])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 81531DiisopropylethylamineHCID 67184206HCID 67184206, compound

Product 1

HCID 86615226Acetic acid [benzyl-(2-oxo-ethyl)carbamoyl]methyl esterYield 57%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
-15 °C

Procedure

Acetic acid [benzyl-(2-hydroxyethyl)carbamoyl]methyl ester (1.28 g, 5.10 mmol) was weighed into a 200 mL round bottom flask and purged with nitrogen. Dichloromethane (50 mL) was added, and the reaction was cooled to −15° C. for 10 minutes. Dimethylsulfoxide (3.61 mL, 51.0 mmol), N,N-diisopropylethylamine (4.43 mL, 25.5 mmol), and pyridine sulfur trioxide complex (4.06 g, 25.5 mmol) were then added sequentially at −15° C. The reaction was allowed to warm slowly to room temperature and stirred overnight. The reaction was complete by thin layer chromatography, and was diluted with ethyl acetate. The organic solution was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride. The organic layer was separated and dried over anhydrous magnesium sulfate. The drying agent was removed via filtration and solvent was removed in vacuo to give crude title compound as a yellow oil. The crude material was chromatographed on silica gel using 1:1 ethyl acetate:dichloromethane as the mobile phase. Fractions were combined and solvent was removed in vacuo to give pure title compound as a colorless oil (0.72 g, 57% yield). (m/z): [M+H]+ calcd for C13H15NO4 250.11, found 250.0.

Workup

  1. custompurged with nitrogen
  2. additionDichloromethane (50 mL) was added
  3. temperatureto warm slowly to room temperature
  4. washThe organic solution was washed with saturated aqueous sodium bicarbonate and saturated aqueous sodium chloride
  5. customThe organic layer was separated
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe drying agent was removed via filtration and solvent
  8. customwas removed in vacuo
  9. customto give crude title compound as a yellow oil
  10. customThe crude material was chromatographed on silica gel using 1:1 ethyl acetate
  11. customsolvent was removed in vacuo

Sources & evidence

ORD record
ord-9a0dd54b81ca4f3ab6dfb059532c2d83
Source dataset
uspto-grants-2015_01
Patent number
US08927573B2

Reaction notes

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