m-Chloroperbenzoic acid → 2-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane

HRID 1019025Notes

Reaction equation

HRID 1019025 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:20]=[CH2:21])[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClC1C=C(C=CC=1)C(OO)=[O:27]>CCOC(C)=O>[CH2:1]([O:8][C:9]([NH:11][CH:12]([CH:20]1[O:27][CH2:21]1)[CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 70297m-Chloroperbenzoic acidHCID 136065862-Benzyloxycarbonylamino-1-phenyl-3-butene

Product 1

HCID 148872432-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 2-benzyloxycarbonylamino-1-phenyl-3-butene (1.43 g, 5.08 mmoles) in 20 mL of CH2C12 was added 3-chloroperoxybenzoic acid (2.19 g, 60%, 7.62 mmoles) in several portions, and the mixture was stirred at room temperature for 30 hrs. After addition of EtOAc (60 mL), the mixture was washed with saturated NaHCO3 and brine, and the organic layer was dried over Na2SO4. Evaporation of the solvent afforded an oily residue. The crude product was purified by column chromatography on silica gel with elution by 2:8 EtOAc-hexane to give pure 2-benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane.

Workup

  1. washthe mixture was washed with saturated NaHCO3 and brine
  2. dry with materialthe organic layer was dried over Na2SO4
  3. customEvaporation of the solvent
  4. customafforded an oily residue
  5. customThe crude product was purified by column chromatography on silica gel with elution by 2:8 EtOAc-hexane

Sources & evidence

ORD record
ord-6f7b2463c5af4d069db17477e0f3d9e0
Source dataset
uspto-grants-2002_11
Patent number
US06486180B1

Reaction notes

Loading…