Acetone → HCID 53249126, compound

HRID 1512357Notes

Reaction equation

HRID 1512357 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 (1×500 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 (1×500 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated
  4. washFlash chromatography (gradient elution; 25% ethyl acetate/hexanes to 50%)

Sources & evidence

ORD record
ord-bc5ede5bca78436aba3ea5ca3b65fd40
Source dataset
uspto-grants-2012_07
Patent number
US08217067B2

Reaction notes

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