Dimethyl Sulfoxide → HCID 86675619, compound

HRID 1844569Notes

Reaction equation

HRID 1844569 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH:13]([CH3:31])[CH2:14][CH2:15][N:16]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18].C(N(CC)CC)C>C(Cl)Cl>[CH3:31][CH:13]([CH:12]=[O:11])[CH2:14][CH2:15][N:16]([C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 86675620HCID 86675620, compound

Product 1

HCID 86675619HCID 86675619, compoundYield 34.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

Dimethyl sulfoxide (5.17 mL) was added to a solution of oxalyl chloride (3.12 mL) in methylene chloride (70 mL) with stirring at −78° C., and the mixture was stirred at the same temperature for 5 minutes. Then, a solution of the crude product of di-tert-butyl (4-hydroxy-3-methylbutyl)imidodicarbonate (19.8 g) in methylene chloride (50 mL) was added thereto. The mixture was stirred at the same temperature for 15 minutes. Then, triethylamine (13.4 mL) was added thereto, and the mixture was heated to room temperature and stirred. The reaction solution was separated into aqueous and organic layers by the addition of water. The organic layer was washed with water and saturated sodium chloride solution and then dried over anhydrous sodium sulfate. After filtration and concentration under reduced pressure, the obtained crude product was purified by silica gel column chromatography to obtain the title compound (6.75 g).

Workup

  1. stirringthe mixture was stirred at the same temperature for 5 minutes
  2. stirringThe mixture was stirred at the same temperature for 15 minutes
  3. temperaturethe mixture was heated to room temperature
  4. stirringstirred
  5. customThe reaction solution was separated into aqueous and organic layers
  6. additionby the addition of water
  7. washThe organic layer was washed with water and saturated sodium chloride solution
  8. dry with materialdried over anhydrous sodium sulfate
  9. filtrationAfter filtration and concentration under reduced pressure
  10. customthe obtained crude product
  11. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-9ae026a9054748d69ae0b1e19ac4e12b
Source dataset
uspto-grants-2015_02
Patent number
US08946443B2

Reaction notes

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