Ethyl Acetate → 2-Benzyloxycarbonylamino-1-phenyl-3,4-epoxy-butane

HRID 2270081Notes

Reaction equation

HRID 2270081 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>C(Cl)Cl>[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

5

Reactant 3

HCID 8857Ethyl AcetateHCID 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 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-benzyloxycarbonylamino-1-phenyl-3-butene (1.43 g, 5.08 mmoles) in 20 mL of CH2Cl2 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-22955231db1b4284a78377a5b6cea0cd
Source dataset
uspto-grants-2001_12
Patent number
US06331541B1

Reaction notes

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