Hydrogen Peroxide → 2-(4-{2-[2-(4-Carbamoylphenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic Acid Ethyl Ester

HRID 898437Notes

Reaction equation

HRID 898437 reaction equation
[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30]#[N:31])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:11][CH:10]=1)([CH3:7])[CH3:6])[CH3:2].C(=O)([O-])[O-:34].[K+].[K+].OO>CS(C)=O>[CH2:1]([O:3][C:4](=[O:32])[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][CH2:16][CH2:17][C:18]2[N:19]=[C:20]([C:24]3[CH:29]=[CH:28][C:27]([C:30](=[O:34])[NH2:31])=[CH:26][CH:25]=3)[O:21][C:22]=2[CH3:23])=[CH:13][CH:14]=1)([CH3:7])[CH3:6])[CH3:2]

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 11430Potassium CarbonateHCID 235900232-(4-{2-[2-(4-Cyanophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic Acid Ethyl Ester

Product 1

HCID 235900242-(4-{2-[2-(4-Carbamoylphenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic Acid Ethyl EsterYield 93%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
0 °C

Procedure

2-(4-{2-[2-(4-Cyanophenyl)-5-methyloxazol-4-yl]ethoxy}phenoxy)-2-methylpropionic acid ethyl ester (60 mg, 0.14 mmol) and potassium carbonate (30 mg, excess) were dissolved in dimethylsulfoxide (1 mL). After cooling to 0° C., the mixture was treated with hydrogen peroxide (120 •L of a 30% aqueous solution) and then warmed to ambient temperature. After stirring for 1 h, the mixture was partitioned between EtOAc (15 mL) and H2O. The aqueous phase was extracted with EtOAc (3×), and then the combined organic phases were dried (MgSO4), filtered and concentrated to provide the product as a white solid (58 mg, 93%): mp 112° C.; 1H NMR (400 MHz, CDCl3) δ 8.05 (d, J=8.4 Hz, 2H), 7.87 (d, J=8.4 Hz, 2H), 6.81-6.77 (m, 4H), 6.12 (br s, 1H), 5.66 (br s, 1H), 4.22 (q, J=6.8 Hz, 2H), 4.18 (t, J=6.4 Hz, 2H), 2.95 (t, J=6.4 Hz, 2H), 2.38 (s, 3H), 1.52 (s, 6H), 1.27 (t, J=7.2 Hz, 3H); MS (EI) 475.2 (M+Na)+, 453.2 (M+H)+.

Workup

  1. temperaturethen warmed to ambient temperature
  2. customthe mixture was partitioned between EtOAc (15 mL) and H2O
  3. extractionThe aqueous phase was extracted with EtOAc (3×)
  4. dry with materialthe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-9d1b1a2e757f48b893efa4f9c8a5f3e9
Source dataset
uspto-grants-2008_04
Patent number
US07351728B2

Reaction notes

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