Potassium Persulfate → HCID 86654010, compound

HRID 1947868Notes

Reaction equation

HRID 1947868 reaction equation
[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C:4](=[C:5](/[CH:20]=C/C3C=CC=CC=3)[CH:6]=[CH:7][C:8]=2[NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH2:3]1.S(OOS([O-])(=O)=O)([O-])(=O)=[O:29].[K+].[K+].[O-]S([O-])=O.[Na+].[Na+]>CN(C=O)C>[CH:20]([C:5]1[CH:6]=[CH:7][C:8]([NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:16])[CH3:17])=[C:9]2[C:4]=1[CH2:3][N:2]([CH3:1])[C:10]2=[O:11])=[O:29]

Participants

5

Reactant 3

HCID 24412Potassium PersulfateHCID 24437Sodium SulfiteHCID 86654011HCID 86654011, compound2×

Product 1

HCID 86654010HCID 86654010, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

tert-Butyl {2-methyl-3-oxo-7-[(E)-2-phenylethenyl]-2,3-dihydro-1H-isoindol-4-yl}carbamate (Compound 109D, 1.0E2 mg, 0.27 mmol) was added in one portion to a pre-stirred mixture (room temperature, 45 min) of potassium osmate dihydrate (1.0 mg, 0.0027 mmol) and potassium monopersulfate (170 mg, 1.1 mmol) in DMF (1.35 mL). After stirring overnight at room temperature, the reaction mixture was treated with 1.35 mL of saturated aqueous Na2SO3. The resulting slurry was extracted with EtOAc (3×) and the combined organic layers were washed with 1N HCl (3×) and brine and concentrated in vacuo. The desired product was obtained after chromatography using an ISCO Combiflash unit (0-15% EtOAc in Heptane) as 23 mg of a tan solid (29% yield). 1H NMR (400 MHz, DMSO-d6) δ=1.51 (s, 9H), 3.08 (s, 3H), 4.74 (s, 2H), 8.12 (d, J=8.6 Hz, 1H), 8.21 (d, J=8.6 Hz, 1H), 9.95 (s, 1H), 10.01 (s, 1H). MS (ES+): m/z 291.28 (100) [MH+]; HPLC: tR=1.27 min (UPLC, Analytical).

Workup

  1. extractionThe resulting slurry was extracted with EtOAc (3×)
  2. washthe combined organic layers were washed with 1N HCl (3×) and brine
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cc1eafb28349445ebc7c294cc0ec6d2d
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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