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

HRID 1351850노트

반응식

HRID 1351850 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-150d3487d6e641b299c8e750d1ae46a1
출처 데이터셋
uspto-grants-2007_05
특허 번호
US07217706B2

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