Sodium Bicarbonate → HCID 10695920, compound

HRID 1489436Notes

Reaction equation

HRID 1489436 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:39])(C[Si](OC(C)C)(C)C)[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:22]=[CH:21][C:20]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])=[CH:19][CH:18]=2)[C:13]1=[O:30])[CH3:11].[C:40](=O)([O-])[OH:41].[Na+]>CO.O1CCCC1.OO>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:39])([CH2:40][OH:41])[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][C:24]([F:29])([F:28])[CH:25]([F:26])[F:27])=[CH:21][CH:22]=2)[C:13]1=[O:30])[CH3:11]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 10674685HCID 10674685, compound

Product 1

HCID 10695920HCID 10695920, compoundYield 69%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[(1R,2S)-2-(2,4-Difluorophenyl)-2-hydroxy-3-(isopropoxydimethylsilyl)-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (0.88 g) was dissolved in a mixture of methanol and tetrahydrofuran (1:1, 10 ml), to which 1.57 ml of 30% aqueous hydrogen peroxide and 0.128 g of sodium hydrogencarbonate were added. The mixture was heated at 70° to 80° C. for 90 minutes, cooled and extracted with 50 ml of ethyl acetate. The extract was washed with 25 ml of water, an aqueous solution of Na2S2O3 (25 ml×2) and 25 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography (silica gel: 50 g, eluent; hexane:ethyl acetate=2:3) and recrystallized from diisopropyl ether to give 0.5 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (yield: 69%) as colorless powdery crystals.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated at 70° to 80° C. for 90 minutes
  3. temperaturecooled
  4. extractionextracted with 50 ml of ethyl acetate
  5. washThe extract was washed with 25 ml of water
  6. dry with materialan aqueous solution of Na2S2O3 (25 ml×2) and 25 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography (silica gel: 50 g, eluent; hexane:ethyl acetate=2:3)
  9. customrecrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-eb9533b3cf574e6294b84bb06aa1356d
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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