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

HRID 1793664

反応式

HRID 1793664 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
0 °C

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-235e9784afc141d3be6661cba6cb882e
出典データセット
uspto-grants-2006_07
特許番号
US07081538B1

関連ノート

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