Potassium Carbonate → 2-(3-(2-(5-Methyl-2-phenyloxazol-4-yl)ethylthio)phenyl)acetic acid

HRID 1822730

Reaction equation

HRID 1822730 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14]Br.[SH:16][C:17]1[CH:18]=[C:19]([CH2:23][C:24]([OH:26])=[O:25])[CH:20]=[CH:21][CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][S:16][C:17]1[CH:18]=[C:19]([CH2:23][C:24]([OH:26])=[O:25])[CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 35431562-(3-Mercaptophenyl)acetic acidHCID 156164424-(2-Bromoethyl)-5-methyl-2-phenyloxazole

Product 1

HCID 221698462-(3-(2-(5-Methyl-2-phenyloxazol-4-yl)ethylthio)phenyl)acetic acid

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2-(5-methyl-2-phenyloxazol-4-yl)ethylbromide (136 mg) and 3-mercaptophenylacetic acid.methyl ester (78 mg) were dissolved in acetonitrile (5 ml) and thereto was added potassium carbonate and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into ice water and the mixture was extracted with ether. The extract was washed with an aqueous solution of sodium hydroxide, water and a saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=200:1→50:1) to give the compound of the present invention (92 mg) having the following physical data.

Workup

  1. extractionthe mixture was extracted with ether
  2. washThe extract was washed with an aqueous solution of sodium hydroxide, water
  3. dry with materiala saturated aqueous solution of sodium chloride, successively, dried over anhydrous magnesium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography on silica gel (chloroform:ethyl acetate=200:1→50:1)
  6. customto give the compound of the present invention (92 mg)

Sources & evidence

ORD record
ord-e64951fedac248b5a1c2df2c983bd553
Source dataset
uspto-grants-2006_05
Patent number
US07037914B2

Linked notes

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