Hydrogen Peroxide → HCID 10602929, compound

HRID 609892Notes

Reaction equation

HRID 609892 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23][N:24]([CH3:37])[CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]4[O:34][CH2:35][O:36][C:30]=4[CH:29]=3)[C:19](=[O:38])[CH2:18][S:17]2)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].OO.C(OCC)(=[O:43])C.C(=O)([O-])[O-].[Na+].[Na+]>C(O)(=O)C>[C:12]([C:9]1[CH:8]=[C:7]([CH:16]2[N:20]([CH2:21][CH2:22][CH2:23][N:24]([CH3:37])[CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]4[O:34][CH2:35][O:36][C:30]=4[CH:29]=3)[C:19](=[O:38])[CH2:18][S:17]2=[O:43])[CH:6]=[C:5]([C:1]([CH3:2])([CH3:3])[CH3:4])[C:10]=1[OH:11])([CH3:14])([CH3:15])[CH3:13]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 8857Ethyl AcetateHCID 10340Sodium CarbonateHCID 9850335HCID 9850335, compound

Product 1

HCID 10602929HCID 10602929, compoundYield 39%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-(3,5-di-tert-butyl-4-hydroxyphenyl)-3-[3-[N-methyl-N-[2-(3,4-methylenedioxy-phenoxy)-ethyl]amino]propyl]-1,3-thiazolidin-4-one (0.30 g) obtained in Example 26-A or 26-B in acetic acid (5 ml) was added 35% aqueous solution of hydrogen peroxide (0.20 g), and the mixture was stirred at room temperature overnight. After completion of the reaction, the reaction mixture was added to a mixture of ethyl acetate and a 5% aqueous solution of sodium carbonate and stirred. The organic layer was separated, dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2) to afford 0.12 g (39%) of the title compound as a colorless oil. MS (m/z): 558 (M+) NMR (CDCl3) (200 MHz) δ: 1.41 (18H, s), 1.4-2.0 (2H, m), 2.28 (3H, s), 2.3-2.7 (2H, m), 2.72 (2H, t, J=5.7 Hz), 2.9-3.2 (1H, m), 3.37 and 3.69 (2H, ABq, J=16 Hz), 3.8-4.2 (3H, m), 5.40 (1H, s), 5.61 (1H, s), 5.87 (2H, s), 6.1-6.8 (3H, m), 6.94 (2H, s)

Workup

  1. customAfter completion of the reaction
  2. customThe organic layer was separated
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (eluent; chloroform-methanol, 98:2)

Sources & evidence

ORD record
ord-f4ce20aad548434d8ed8a9cd1e671133
Source dataset
uspto-grants-1999_12
Patent number
US05998452

Reaction notes

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