Water → HCID 67546517, compound

HRID 2356722Notes

Reaction equation

HRID 2356722 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:21]3[CH:25]=[CH:24][S:23][CH:22]=3)=[C:11]([C:13]([CH3:20])([CH3:19])[C:14]([O:16]CC)=[O:15])[N:12]=2)=[CH:4][CH:3]=1.B(Br)(Br)Br.O.C(OCC)(=O)C>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([C:21]3[CH:25]=[CH:24][S:23][CH:22]=3)=[C:11]([C:13]([CH3:20])([CH3:19])[C:14]([OH:16])=[O:15])[N:12]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 25134Boron tribromide2×HCID 67547778HCID 67547778, compound

Product 1

HCID 67546517HCID 67546517, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-[2-(4-fluorophenyl)-5-(3-thienyl)-oxazol-4-yl]-2-methylpropionate (54 mg) in methylene chloride (3 ml) was added boron tribromide (0.45 ml, 1.0M methylene chloride solution) under ice-cooling, and the mixture was allowed to warm to room temperature. To the mixture, another portion of boron tribromide (1.05 ml, 1.0M methylene chloride solution) was added to the mixture, and the resulting mixture was stirred at room temperature for 18 hours. To the reaction mixture were added water and ethyl acetate, the organic layer was collected, washed with brine and dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=15:1) to obtain 2-[2-(4-fluorophenyl)-5-(3-thienyl)oxazol-4-yl]-2-methylpropionic acid (32 mg). The product was dissolved in methanol, sodium methoxide (0.19 ml, 0.5M methanol solution) was added to the solution and after the mixture was stirred for 10 minutes, the solvent was removed under reduced pressure. The resulting residue was triturated with acetone to obtain sodium 2-[2-(4-fluorophenyl)-5-(3-thienyl)oxazol-4-yl]-2-methyl-propionate (30 mg) as pale brownish powder.

Workup

  1. temperaturecooling
  2. customthe organic layer was collected
  3. washwashed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (solvent: chloroform:methanol=15:1)

Sources & evidence

ORD record
ord-37aa4d2b6380478a841f866a7ece80db
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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