m-Chloroperbenzoic acid → 1-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropane

HRID 1351850Notes

Reaction equation

HRID 1351850 reaction equation
[CH2:1]([N:4]([C:11]([O:13][CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:12])[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)[CH:2]=[CH2:3].ClC1C=CC=C(C(OO)=[O:29])C=1.S([O-])(O)=O.[Na+]>ClCCl>[CH2:14]([O:13][C:11]([N:4]([CH2:1][CH:2]1[O:29][CH2:3]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:12])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 11448535benzyl N-phenyl-N-(prop-2-en-1-yl)carbamateHCID 23665763Sodium Bisulfite

Product 1

HCID 180073081-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropaneYield 37.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under nitrogen, to a solution of N-allyl-N-phenyl-benzyloxycarbonylamine (5.5 g) in dichloromethane (50 ml) was added m-chloroperbenzoic acid (3.9 g) at 5° C., and the mixture was stirred at room temperature for 3 days. The resulting mixture was poured into aqueous sodium hydrogensulfite and extracted with ethyl acetate. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1) to give 1-(N-benzyloxycarbonyl-N-phenylamino)-2,3-epoxypropane (2.2 g).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was successively washed with saturated aqueous sodium hydrogencarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=10:1 to 5:1)

Sources & evidence

ORD record
ord-150d3487d6e641b299c8e750d1ae46a1
Source dataset
uspto-grants-2007_05
Patent number
US07217706B2

Reaction notes

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