Acetone → HCID 53249126, compound

HRID 1035102Notes

Reaction equation

HRID 1035102 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-26ba95c6970b4faebb842db95fdc9468
Source dataset
uspto-grants-2013_10
Patent number
US08546374B2

Reaction notes

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