Sodium Bicarbonate → HCID 10599948, compound

HRID 1489442Notes

Reaction equation

HRID 1489442 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:38])(C[Si](OC(C)C)(C)C)[C@H:9]([N:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:21]=[CH:20][C:19]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])=[CH:18][CH:17]=2)[C:12]1=[O:29])[CH3:10].[C:39](=O)([O-])[OH:40].[Na+]>CO.O1CCCC1.OO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C@@:8]([OH:38])([CH2:39][OH:40])[C@H:9]([N:11]1[CH:15]=[CH:14][N:13]([C:16]2[CH:17]=[CH:18][C:19]([O:22][C:23]([F:28])([F:27])[CH:24]([F:26])[F:25])=[CH:20][CH:21]=2)[C:12]1=[O:29])[CH3:10]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 10816661HCID 10816661, compound

Product 1

HCID 10599948HCID 10599948, compoundYield 60.3%

Reagents, catalysts & solvents 3

HCID 784Hydrogen PeroxideSolventHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

1-[(1R,2S)-2-(2-Fluorophenyl)-2-hydroxy-3-(isopropoxydimethylsilyl)-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (5.5 g) was dissolved in a mixture of methanol and tetrahydrofuran (1:1, 50 ml), to which 10 ml of 30% aqueous hydrogen peroxide and 0.82 g of sodium hydrogencarbonate were added. The mixture was heated at 80° to 85° C. for 2 hours. The reaction solution was cooled and extracted with 200 ml of ethyl acetate. The extract was washed with 100 ml of water, an aqueous solution of Na2S2O3 (100 ml×2) and 100 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate. The solvent was distilled off under reduced pressure. The residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=1:1) and recrystallized from a mixture of methanol and diisopropyl ether to give 2.7 g of 1-[(1R,2S)-2-(2-fluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(1,1,2,2-tetrafluoroethoxy)phenyl]-2(1H,3H)-imidazolone (yield: 60%) as colorless powdery crystals.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated at 80° to 85° C. for 2 hours
  3. temperatureThe reaction solution was cooled
  4. extractionextracted with 200 ml of ethyl acetate
  5. washThe extract was washed with 100 ml of water
  6. dry with materialan aqueous solution of Na2S2O3 (100 ml×2) and 100 ml of an aqueous solution of sodium chloride successively, and dried over magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe residue was purified by silica gel chromatography (eluent; hexane:ethyl acetate=1:1)
  9. customrecrystallized from a mixture of methanol and diisopropyl ether

Sources & evidence

ORD record
ord-0734b6a5049d43ac9df4d4969f26a333
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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