Hydrogen Peroxide → HCID 86746867, compound

HRID 249272Notes

Reaction equation

HRID 249272 reaction equation
[C:1]1([S:7]/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH:25]O>C(O)(=O)C.O>[C:1]1([S:7](/[CH:8]=[CH:9]/[C:10]([NH:12][C@@H:13]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])=[O:11])=[O:25])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 784Hydrogen PeroxideHCID 86746868HCID 86746868, compound

Product 1

HCID 86746867HCID 86746867, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

Diethyl N-[3-phenylthio-2(E)-propenoyl]-(R)-aspartate (3.51 g, 10 mmol) was dissolved in glacial acetic acid (30 ml) and a 30% solution of hydrogen peroxide (1.4 ml) was added and the mixture was stirred at room temperature for 36 hours, then diluted with water (100 ml) and extracted twice with dichloromethane (50 ml each). The organic phase was dried over anhydrous sodium sulfate, the solvents were evaporated and the residue was suspended in carbon tetrachloride and filtered to give a crude product which was recrystallised from toluene, yielding the desired product (2.3 g, 63%).

Workup

  1. extractionextracted twice with dichloromethane (50 ml each)
  2. dry with materialThe organic phase was dried over anhydrous sodium sulfate
  3. customthe solvents were evaporated
  4. filtrationfiltered
  5. customto give a crude product which
  6. customwas recrystallised from toluene

Sources & evidence

ORD record
ord-fda1020981d14dd484e399916e51563c
Source dataset
uspto-grants-1993_05
Patent number
US05214045

Reaction notes

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