Sodium Bicarbonate → HCID 67196687, compound

HRID 547447Notes

Reaction equation

HRID 547447 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][N:14]=3)=[C:11]([NH:19][C:20](=[O:32])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28]COC)[O:10][N:9]=2)=[CH:4][CH:3]=1.S([O-])(O)(=O)=O.[Na+].C(=O)([O-])O.[Na+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:12]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][N:14]=3)=[C:11]([NH:19][C:20](=[O:32])[CH2:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[OH:28])[O:10][N:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 516919Sodium BisulfateHCID 67196384HCID 67196384, compound

Product 1

HCID 67196687HCID 67196687, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Fifty (50) mg of 3-(4-fluorophenyl)-5-[(2-methoxymethoxy-phenyl)acetylamino]-4-(4-pyrimidinyl)isoxazole was dissolved in 30 mL of dichloromethane and into which 460 mg of sodium hydrogensulfate reagent as fixed on silica gel was added, followed by 4 hours' stirring at room temperature. After addition of saturated aqueous sodium hydrogencarbonate solution, the reaction solution was extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate and from which the solvent was distilled off under reduced pressure. Thus obtained residue was washed with ether-hexane to provide 16 mg (yield: 34%) of the title compound.

Workup

  1. additionwas added
  2. extractionthe reaction solution was extracted with chloroform
  3. extractionThe chloroform extract
  4. dry with materialwas dried over anhydrous magnesium sulfate and from which the solvent
  5. distillationwas distilled off under reduced pressure
  6. washThus obtained residue was washed with ether-hexane

Sources & evidence

ORD record
ord-56d3f9dc13eb4014983e54c5b3cb98be
Source dataset
uspto-grants-2011_05
Patent number
US07939536B2

Reaction notes

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