Dimethyl Sulfoxide → HCID 66781796, compound

HRID 1096474Notes

Reaction equation

HRID 1096474 reaction equation
[CH2:1]([O:3][C:4](=[O:37])[CH:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([NH:14][C:15](=[O:36])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]3[CH2:29][N:28]([CH3:30])[C:27]4[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=4[O:25]3)=[CH:18][C:17]=2[Cl:35])[CH:8]=1)[OH:6])[CH3:2].C(N(C(C)C)CC)(C)C.CS(C)=O.C(OCC)(=O)C>O>[CH2:1]([O:3][C:4](=[O:37])[C:5]([C:7]1[CH:12]=[CH:11][C:10]([Cl:13])=[C:9]([NH:14][C:15](=[O:36])[C:16]2[CH:21]=[CH:20][C:19]([O:22][CH2:23][C@@H:24]3[CH2:29][N:28]([CH3:30])[C:27]4[CH:31]=[CH:32][CH:33]=[CH:34][C:26]=4[O:25]3)=[CH:18][C:17]=2[Cl:35])[CH:8]=1)=[O:6])[CH3:2]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 86609829HCID 86609829, compound

Product 1

HCID 66781796HCID 66781796, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under argon atmosphere, to a mixture of the compound (159 mg) prepared in Example 31, diisopropylethylamine (0.30 mL), dimethylsulfoxide (2 mL), and ethyl acetate (4 mL), sulfur trioxide pyridine complex (139 mg) were added at ice-cold temperature, and the mixture was stirred for 1 hour at the same temperature. Water was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with water and saturated brine solution and was dried by anhydrous magnesium sulphate. The title compound (104 mg) having the following physical data was obtained by purifying the residue obtained by removing the solvent by silica gel column chromatography (n-hexane:ethyl acetate=3:1→2:1).

Workup

  1. additionwere added at ice-cold temperature
  2. extractionwas extracted with ethyl acetate
  3. washThe organic layer was washed with water and saturated brine solution
  4. dry with materialwas dried by anhydrous magnesium sulphate
  5. customwas obtained
  6. customby purifying the residue
  7. customobtained
  8. customby removing the solvent by silica gel column chromatography (n-hexane:ethyl acetate=3:1→2:1)

Sources & evidence

ORD record
ord-40e06e80da79415c80263b528891d6e1
Source dataset
uspto-grants-2012_03
Patent number
US08138335B2

Reaction notes

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