Sodium Bicarbonate → HCID 11799245, compound

HRID 1489432Notes

Reaction equation

HRID 1489432 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C@@:9]([OH:40])([CH2:32][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][CH2:24][C:25]([F:30])([F:29])[CH:26]([F:28])[F:27])=[CH:19][CH:18]=2)[C:13]1=[O:31])[CH3:11].C(=O)([O-])[OH:42].[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:40])([CH2:32][OH:42])[C@H:10]([N:12]1[CH:16]=[CH:15][N:14]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][C:25]([F:29])([F:30])[CH:26]([F:28])[F:27])=[CH:21][CH:22]=2)[C:13]1=[O:31])[CH3:11]

Participants

6

Reactant 2

HCID 516892Sodium BicarbonateHCID 10603495HCID 10603495, compound

Product 1

HCID 11799245HCID 11799245, compoundYield 88.3%

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-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (1.8 g) was dissolved in a mixture of methanol and tetrahydrofuran (1:1, 20 ml), to which 3.21 ml of 30% aqueous hydrogen peroxide and 0.262 g of sodium hydrogencarbonate were added. The mixture was heated at 70° to 80° C. for 90 minutes, cooled and extracted with 100 ml of ethyl acetate. The extract was washed with 50 ml of water, an aqueous solution of Na2S2O3 (50 ml×2) and 50 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 1.32 g of 1-[(1R,2S)-2-(2,4-difluorophenyl)-2,3-dihydroxy-1-methylpropyl]-3-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]-2(1H,3H)-imidazolone (yield: 88%) as colorless prisms.

Workup

  1. additionwere added
  2. temperatureThe mixture was heated at 70° to 80° C. for 90 minutes
  3. temperaturecooled
  4. extractionextracted with 100 ml of ethyl acetate
  5. washThe extract was washed with 50 ml of water
  6. dry with materialan aqueous solution of Na2S2O3 (50 ml×2) and 50 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-fc3f3cf6e067409c8a351acf45159c4c
Source dataset
uspto-grants-1997_10
Patent number
US05677464

Reaction notes

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