Sulfuric Acid → HCID 19882345, compound

HRID 847153Notes

Reaction equation

HRID 847153 reaction equation
[CH3:1][S:2]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([CH2:23][CH2:24][CH2:25][CH2:26][S:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)(=[N:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[O:13])=[CH:8][CH:7]=1)(=[O:4])=[O:3].S(=O)(=O)(O)[OH:35].B1([O-])OO1.O.O.O.O.[Na+]>CO>[N:17]1([CH2:16][CH2:15][N:14]=[S:12]([C:9]2[CH:8]=[CH:7][C:6]([NH:5][S:2]([CH3:1])(=[O:3])=[O:4])=[CH:11][CH:10]=2)([CH2:23][CH2:24][CH2:25][CH2:26][S:27]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)=[O:35])=[O:13])[CH2:18][CH2:19][O:20][CH2:21][CH2:22]1

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 19882362HCID 19882362, compoundHCID 23693097Sodium;3-oxidodioxaborirane;tetrahydrate

Product 1

HCID 19882345HCID 19882345, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A cold (0° C.) solution of S-[4-(methanesulfonylamino)phenyl]-N-[2-(4-morpholinyl)ethyl]-S-[4-(phenylthio)butyl]sulfoximine in methanol is treated slowly with excess 30% sulfuric acid and then sodium perborate tetrahydrate (10 equivalents) is added. The mixture is stirred at 0° C. for 2 hrs and then at ambient temperature for 2 hrs. The methanol is removed in vacuo and the residue basified with 50% sodium hydroxide and filtered. The filter cake is washed with methylene chloride. The aqueous filtrate is extracted with methylene chloride and the extract combined with the methylene chloride used to wash the filter cake. The methylene chloride solution is washed with water, dried and concentrated to obtain the title compound.

Workup

  1. waitat ambient temperature for 2 hrs
  2. customThe methanol is removed in vacuo
  3. filtrationfiltered
  4. washThe filter cake is washed with methylene chloride
  5. extractionThe aqueous filtrate is extracted with methylene chloride
  6. washto wash the filter cake
  7. washThe methylene chloride solution is washed with water
  8. customdried
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6ffb6206c9ac4c999bf5d5582b9227a3
Source dataset
uspto-grants-1992_08
Patent number
US05140026

Reaction notes

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