Hydrogen Peroxide → HCID 22882479, compound

HRID 863291Notes

Reaction equation

HRID 863291 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2([CH:17]=[CH2:18])[CH2:16][CH2:15]2)[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH2:21].[OH-].[Na+].OO>O1CCCC1>[C:1]([O:5][C:6]([N:8]1[C@@H:12]([CH2:13][C:14]2([CH2:17][CH2:18][OH:21])[CH2:15][CH2:16]2)[CH2:11][O:10][C:9]1([CH3:20])[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 14798Sodium HydroxideHCID 22882483HCID 22882483, compound

Product 1

HCID 22882479HCID 22882479, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2.5 ml of diborane-dimethylsulfide complex are added to 18.0 g of 3-tert-butoxycarbonyl-2,2-dimethyl-4(S)-[(1-vinylcyclopropyl)methyl]-1,3-oxazolidine, dissolved in 300 ml of tetrahydrofuran at 0° C. in the course of 3 minutes and the mixture is then stirred for 3 h, while cooling with ice. 5 ml of water, 16 ml of 2N sodium hydroxide solution and 8.5 ml of a 30% hydrogen peroxide solution are added in succession and the mixture is subsequently stirred at room temperature for 1 h. It is then diluted with ice-cold potassium carbonate solution and the aqueous phase is extracted with ethyl acetate. Purification of the crude product is carried out over 900 g of silica gel (mobile phase B): Rf (B)=0.25; anal. calc. for C16H35NO4 : C 64.18%, H 9.76%, N 4.68%; found C 64.05%, H 9.76%, N 4.73%.

Workup

  1. temperaturewhile cooling with ice
  2. stirringthe mixture is subsequently stirred at room temperature for 1 h
  3. additionIt is then diluted with ice-cold potassium carbonate solution
  4. extractionthe aqueous phase is extracted with ethyl acetate
  5. customPurification of the crude product

Sources & evidence

ORD record
ord-4c77691a1d19413c8de47166fcff5b7f
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

Loading…