Hydrogen Peroxide → HCID 44545782, compound

HRID 1891415Notes

Reaction equation

HRID 1891415 reaction equation
[C:1]([C:4]1[C:5]([O:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N:31]=2)=[C:6]([O:15][CH2:16][CH2:17][CH:18]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=2)[CH3:19])[C:7]2[O:11][C:10]([CH3:12])=[N:9][C:8]=2[C:13]=1[CH3:14])(=[O:3])[CH3:2].[OH:36]O>C(O)(=O)C>[C:1]([C:4]1[C:5]([O:27][CH2:28][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][N+:31]=2[O-:36])=[C:6]([O:15][CH2:16][CH2:17][CH:18]([C:20]2[CH:21]=[CH:22][C:23]([F:26])=[CH:24][CH:25]=2)[CH3:19])[C:7]2[O:11][C:10]([CH3:12])=[N:9][C:8]=2[C:13]=1[CH3:14])(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 784Hydrogen PeroxideHCID 44545715HCID 44545715, compound

Product 1

HCID 44545782HCID 44545782, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

To a stirred solution of Example 8) (24 mg, 0.05 mmol) in acetic acid (0.5 mL) at room temperature was added H2O2 (30% aq.) and the solution heated to 100° C. for 23 h. The acetic acid was removed in vacuo and the brown oil partitioned between NaHCO3 (20 mL) and EtOAc (20 mL). The aqueous phase (pH=10) was extracted with EtOAc (2×10 mL). The combined extracts were dried (MgSO4) and concentrated in vacuo. The product was purified by column chromatography (silica gel, hexane/Et2O (1:4) to Et2O to MeOH/DCM (1:19)). The title compound (10 mg, 41%) eluted from the column with MeOH/DCM (1:19) as a pale yellow oil. 1H NMR (CDCl3): δ 8.26-8.24 (m, 1H), 7.41-7.38 (m, 1H), 7.21 (m, 4H), 7.00-6.94 (m, 2H), 4.44 (t, J=6 Hz, 2H), 4.22-4.15 (m, 2H), 3.32 (t, J=6 Hz, 2H), 3.05-2.95 (m, 1H), 2.57 (s, 3H), 3.37 (s, 3H), 2.34 (s, 3H), 2.10-1.90 (m, 2H), 1.30 (d, J=6.9 Hz, 3H), ESIMS m/z [M+H]+ 493.2.

Workup

  1. customThe acetic acid was removed in vacuo
  2. customthe brown oil partitioned between NaHCO3 (20 mL) and EtOAc (20 mL)
  3. extractionThe aqueous phase (pH=10) was extracted with EtOAc (2×10 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customThe product was purified by column chromatography (silica gel, hexane/Et2O (1:4) to Et2O to MeOH/DCM (1:19))
  7. washThe title compound (10 mg, 41%) eluted from the column with MeOH/DCM (1:19) as a pale yellow oil

Sources & evidence

ORD record
ord-a4bd3f66836943d9a8e8d7fb00771d48
Source dataset
uspto-grants-2013_08
Patent number
US08507539B2

Reaction notes

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