Dimethyl Sulfoxide → HCID 59556963, compound

HRID 1967310Notes

Reaction equation

HRID 1967310 reaction equation
C(Cl)(=O)C(Cl)=O.C(=O)=O.CC(C)=O.CS(C)=O.[Cl:18][C:19]1[CH:20]=[C:21]([N:25]([C@@H:33]([CH3:36])[CH2:34][OH:35])[C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:22]=[CH:23][CH:24]=1>C(Cl)Cl.O.C(N(CC)CC)C>[Cl:18][C:19]1[CH:20]=[C:21]([N:25]([C@@H:33]([CH3:36])[CH:34]=[O:35])[C:26](=[O:32])[O:27][C:28]([CH3:29])([CH3:30])[CH3:31])[CH:22]=[CH:23][CH:24]=1

Participants

8

Reactant 4

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 18522661Acetone cardiceHCID 59556991HCID 59556991, compound

Product 1

HCID 59556963HCID 59556963, compoundYield 96.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent3×HCID 8471TriethylamineSolvent

Procedure

A solution of oxalyl chloride (318 mg) in methylene chloride (6 mL) was cooled using dry ice/acetone under a nitrogen atmosphere, and a solution of DMSO (258 mg) in methylene chloride (6 mL) was added. The mixture was stirred at the same temperature for 10 min, a solution of tert-butyl (3-chlorophenyl)[(1S)-2-hydroxy-1-methylethyl]carbamate (500 mg) in methylene chloride (8 mL) was added, and the mixture was stirred at the same temperature for 10 min. Triethylamine (0.925 mL) was added, and the mixture was stirred at the same temperature for 30 min. Water (30 mL) was added, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentration under reduced pressure to give the title compound as a colorless oil (yield: 480 mg, 96%).

Workup

  1. stirringthe mixture was stirred at the same temperature for 10 min
  2. stirringthe mixture was stirred at the same temperature for 30 min
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe obtained organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate, and concentration under reduced pressure

Sources & evidence

ORD record
ord-6faadf3b89ac42e598a87825745c228c
Source dataset
uspto-grants-2013_04
Patent number
US08420694B2

Reaction notes

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