Hydrogen Peroxide → HCID 66789540, compound

HRID 1672275Notes

Reaction equation

HRID 1672275 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:13]3[C:14]([CH:23]=[CH2:24])=[CH:15][C:16]([NH:18][S:19]([CH3:22])(=[O:21])=[O:20])=[CH:17][C:12]=3[O:11][C:10]([CH3:26])([CH3:25])[C:9]2=[O:27])=[CH:4][CH:3]=1.[OH:28]O.[OH-].[Na+].[Cl-].[NH4+]>O1CCCC1>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:13]3[C:14]([CH2:23][CH2:24][OH:28])=[CH:15][C:16]([NH:18][S:19]([CH3:22])(=[O:20])=[O:21])=[CH:17][C:12]=3[O:11][C:10]([CH3:26])([CH3:25])[C:9]2=[O:27])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 25517Ammonium ChlorideHCID 24746295HCID 24746295, compound

Product 1

HCID 66789540HCID 66789540, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent4×

Procedure

To a solution of N-[4-(4-fluorophenyl)-2,2-dimethyl-3-oxo-5-vinyl-3,4-dihydro -2H-1,4-benzoxazin-7-yl]methanesulfonamide (compound obtained in Example 156, 200 mg) in tetrahydrofuran (5 mL) was added 10 M borane-dimethylsulfide complex in tetrahydrofuran (0.03 mL) under ice-cooling, and the mixture was stirred at room temperature for 5 hours. Thereto was further added 10 M borane-dimethylsulfide complex in tetrahydrofuran (0.03 mL), and the mixture was stirred for 15 hours. To the reaction mixture were added successively tetrahydrofuran (5 mL), an aqueous 30% hydrogen peroxide solution (0.6 mL) and an aqueous 2N sodium hydroxide solution (0.77 mL), and the mixture was stirred at room temperature for 3 hours. The reaction mixture was poured to an aqueous saturated ammonium chloride solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and brine, dried over sodium sulfate and concentrated in vacuo. The resultant residue was purified by column chromatography on silica gel (Solvent; chloroform→chloroform/ethyl acetate=100/0→0/100) to give N-[4-(4-fluorophenyl)-5-(2-hydroxyethyl)-2,2-dimethyl-3-oxo-3,4-dihydro-2H-1,4-benzoxazin-7-yl]methanesulfonamide (113 mg) as a colorless powder.

Workup

  1. temperaturecooling
  2. stirringthe mixture was stirred for 15 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe resultant residue was purified by column chromatography on silica gel (Solvent; chloroform→chloroform/ethyl acetate=100/0→0/100)

Sources & evidence

ORD record
ord-17f92f314cff447fa44a69147d33822b
Source dataset
uspto-grants-2011_08
Patent number
US07998956B2

Reaction notes

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