Acetone → HCID 57595178, compound

HRID 1785403Notes

Reaction equation

HRID 1785403 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH:16]([OH:21])[CH2:17][N:18]([CH3:20])[CH3:19])[CH:13]=[CH:12][N:11]3[C:22]=2[C:23]2[CH:28]=[CH:27][N:26]=[C:25](SC)[N:24]=2)=[CH:4][CH:3]=1.CO.O[O:34][S:35]([O-:37])=O.[K+].[CH3:39]C(C)=O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]3[CH:15]=[C:14]([CH:16]([OH:21])[CH2:17][N:18]([CH3:20])[CH3:19])[CH:13]=[CH:12][N:11]3[C:22]=2[C:23]2[CH:28]=[CH:27][N:26]=[C:25]([S:35]([CH3:39])(=[O:37])=[O:34])[N:24]=2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 180AcetoneHCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 57595182HCID 57595182, compound

Product 1

HCID 57595178HCID 57595178, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 mL round bottom flask containing sulfide 42 (720 mg, 1.70 mmol) was charged with methanol (20 mL), then a solution of Oxone (3.14 g, 5.10 mmol) in water (20 mL), then acetone (20 mL). After stirring at room temperature for 12 hours, the reaction was cooled to below −20° C. in a dry ice/isopropanol bath, then SO2 was bubbled in for 5 minutes. The reaction was then concentrated under reduced pressure to remove organic solvent, and the resulting aqueous mixture was neutralized with an aqueous potassium carbonate solution. The resulting aqueous solution was extracted exhaustively into ethyl acetate, and the organic fractions were pooled, dried over MgSO4, filtered, and concentrated under reduced pressure, and the sulfone product was not purified further. Yield of 43: 470 mg (61%). 1H NMR (400 MHz, DMSO-d6) δ 2.30 (s, 6H), 2.49 (m, 2H), 3.47 (s, 3H), 4.85 (m, 1H), 5.60 (m, 1H), 7.25 (d, J=7.4 Hz, 1H), 7.33 (t, J=8.8 Hz, 2H), 7.37 (d, J=5.6 Hz, 1H), 7.71 (m, 3H), 8.80 (d, J=5.6 Hz, 1H), 9.51 (d, J=7.4 Hz, 1H). MS (ESI+) 456.2.

Workup

  1. temperaturethe reaction was cooled to below −20° C. in a dry ice/isopropanol bath
  2. customSO2 was bubbled in for 5 minutes
  3. concentrationThe reaction was then concentrated under reduced pressure
  4. customto remove organic solvent
  5. extractionThe resulting aqueous solution was extracted exhaustively into ethyl acetate
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customthe sulfone product was not purified further

Sources & evidence

ORD record
ord-fcab5d554e6f420f8f6d1c0ac68e61c5
Source dataset
uspto-grants-2009_03
Patent number
US07504501B2

Reaction notes

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