1-Methoxy-3-trimethylsilyloxy-1,3-butadiene → HCID 67627134、化合物

HRID 862395

反応式

HRID 862395 の反応式
C(O[C@H:5]1[NH:8][C:7](=[O:9])[C@@H:6]1[C@H:10]([O:12][Si:13]([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14])[CH3:11])(=O)C.[CH3:20][O:21][CH:22]=[CH:23][C:24]([O:26][Si](C)(C)C)=[CH2:25]>ClCCl.[I-].[Zn+2].[I-]>[Si:13]([O:12][C@@H:10]([C@@H:6]1[C@@H:5]([CH2:25][C:24](=[O:26])[CH:23]=[CH:22][O:21][CH3:20])[NH:8][C:7]1=[O:9])[CH3:11])([C:16]([CH3:17])([CH3:18])[CH3:19])([CH3:14])[CH3:15]

参加物

5

反応物 2

HCID 1010511-Methoxy-3-trimethylsilyloxy-1,3-butadieneHCID 10935078Azetidon

生成物 1

HCID 67627134HCID 67627134、化合物収率 43%

試薬・触媒・溶媒 2

HCID 9883512zinc(II)iodide触媒HCID 6344Dichloromethane溶媒

実験手順

(3R,4R) 4-acetoxy-3-[(1R)-(1-(tert-butyldimethylsilyloxy)ethyl)]azetidin-2-one (2 g, 56.96 mM) was dissolved in dichloromethane (150 ml) at ambient temperature and 4-methoxy-2-trimethylsilyloxybut-1,3-diene (1.5 ml, 7.65 mM) added followed by zinc iodide (2.2 g, 17 mM). The reaction mixture was shielded from light and stirred for 15 hours. The mixture was then washed with a 5% aqueous solution of sodium bicarbonate (30 ml) and then water (30 ml). The organic phase was dried with magnesium sulphate and the solvent evaporated. The residue was purified by chromatography on silica, eluting with ethyl acetate/dichloromethane (1:1) to give (3S,4R) 3-((1R)-1-(tert-butyldimethylsilyloxy)ethyl)-4-(4-methoxy-2-oxobut-3-en-1-yl)azetidin-2-one (0.96 g, 43%).

後処理

  1. washThe mixture was then washed with a 5% aqueous solution of sodium bicarbonate (30 ml)
  2. dry with materialThe organic phase was dried with magnesium sulphate
  3. customthe solvent evaporated
  4. customThe residue was purified by chromatography on silica
  5. washeluting with ethyl acetate/dichloromethane (1:1)

出典と根拠

ORDレコード
ord-6c2c0a33a11a4aa4bc833b045bdf3143
出典データセット
uspto-grants-1998_02
特許番号
US05719139

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