Tetrahydrofuran → HCID 21088583, compound

HRID 350755Notes

Reaction equation

HRID 350755 reaction equation
[N:1]1([C:10]2[O:11][C:12]([CH2:22][CH2:23][C:24]([N:26]3[CH2:30][CH2:29][S:28][CH2:27]3)=[O:25])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:14]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1.[O:31]1CCCC1.ClC1C=CC=C(C(OO)=O)C=1>O>[N:1]1([C:10]2[O:11][C:12]([CH2:22][CH2:23][C:24]([N:26]3[CH2:30][CH2:29][S:28](=[O:31])[CH2:27]3)=[O:25])=[C:13]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][CH:16]=3)[N:14]=2)[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 70297m-Chloroperbenzoic acidHCID 21088584HCID 21088584, compound

Product 1

HCID 21088583HCID 21088583, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a mixture of 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propanoyl}thiazolidine (25 mg) and tetrahydrofuran (10 mL) was added m-chloroperbenzoic acid (14.4 mg) with stirring under ice-cooling, and the mixture was stirred overnight at room temperature. The reaction mixture was poured into water, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate and then with saturated brine, dried (MgSO4) and concentrated. The residue was introduced into preparative HPLC and purified to give 3-{3-[2-(1H-benzoimidazol-1-yl)-4-(4-chlorophenyl)-5-oxazolyl]propanoyl}thiazolidine-1-oxide (7.3 mg, yield 28%).

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred overnight at room temperature
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated aqueous sodium hydrogen carbonate
  5. dry with materialwith saturated brine, dried (MgSO4)
  6. concentrationconcentrated
  7. additionThe residue was introduced into preparative HPLC
  8. custompurified

Sources & evidence

ORD record
ord-8ffef582733145bda6fc92c2d4f1c07e
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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