Allyl bromide → N-Allyl-3-(t-Butoxycarbonylamino)isoxazole

HRID 1793664

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HRID 1793664 반응식
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:13]=[CH:12][O:11][N:10]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:16](Br)[CH:17]=[CH2:18]>C(COC)OC.O>[CH2:18]([N:10]1[CH:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:13]=[CH:12][O:11]1)[CH:17]=[CH2:16]

참가 물질

6

반응물 3

HCID 7841Allyl bromideHCID 24758Sodium hydrideHCID 21992950tert-Butyl 1,2-oxazol-3-ylcarbamate

생성물 1

HCID 22022967N-Allyl-3-(t-Butoxycarbonylamino)isoxazole수율 99.6%

시약·촉매·용매 2

HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
0 °C

실험 절차

3-(t-Butoxycarbonylamino)isoxazole (12 g, 65.2 mM) was dissolved in dimethoxyethane (150 ml) and cooled to 0° C. under nitrogen. To the stirred solution was added sodium hydride (60% in oil, 2.87 g, 71.7 mM), and the mixture stirred 20 minutes. Allyl bromide (8.7 g, 71.7 mM) was added dropwise, and the mixture stirred at ambient temperature for 18 hours, then diluted with water (300 ml), and extracted into diethyl ether (3×100 ml). The extracts were washed with brine (100 ml), dried (magnesium sulfate), and chromatographed on silica (50 g) eluting with dichloromethane . Relevant fractions were combined to give the desired product as an oil (14.68 g). MS (ESP): 225 (MH+) for C11H16N2O3

후처리

  1. stirringthe mixture stirred at ambient temperature for 18 hours
  2. extractionextracted into diethyl ether (3×100 ml)
  3. washThe extracts were washed with brine (100 ml)
  4. dry with materialdried (magnesium sulfate)
  5. customchromatographed on silica (50 g)
  6. washeluting with dichloromethane

출처 및 근거

ORD 기록
ord-235e9784afc141d3be6661cba6cb882e
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07081538B1

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