Acetone → HCID 53249126, compound

HRID 645655Notes

Reaction equation

HRID 645655 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2SC)=[N:12][N:11]=[N:10]1.O[O:25][S:26]([O-:28])=O.[K+].[CH3:30]C(C)=O>C(OCC)(=O)C>[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][CH:5]=[CH:4][C:3]=1[N:9]1[C:13]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[S:26]([CH3:30])(=[O:28])=[O:25])=[N:12][N:11]=[N:10]1

Participants

5

Reactant 3

HCID 180AcetoneHCID 11523472HCID 11523472, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 53249126HCID 53249126, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

The product of Example 20 (0.14 g, 0.39 mmol) was dissolved in 10 mL acetone and treated with OXONE (0.94 g, 1.54 mmol) for 24 h. The resulting slurry was taken up in 100 mL ethyl acetate and washed with water (3×50 mL), brine (1×50 mL), dried (MgSO4) and concentrated. Flash chromatography (gradient elution; 25% ethyl acetate/hexanes to 50%) gave 0.08 g of the title compound as a white solid. MS (ESI/NH3) m/z 397 (M+H)+

Workup

  1. washwashed with water (3×50 mL), brine (1×50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washFlash chromatography (gradient elution; 25% ethyl acetate/hexanes to 50%)

Sources & evidence

ORD record
ord-6f22e7d0912444fca8053cb1ffcdb09a
Source dataset
uspto-grants-2010_04
Patent number
US07704997B1

Reaction notes

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