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Benzyl acetate → N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl 2-hydroxypropyl)-azetidin-2-one

HRID 1154915
ノート
印刷プレビュー

反応式

HRID 1154915 の反応式
[C:1]([O:4][CH2:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)(=[O:3])[CH3:2].C([N-]C(C)C)(C)C.[Li+].[Si:20]([N:27]1[CH:30]([CH2:31][CH:32]=[O:33])[CH:29]([N:34]=[N+:35]=[N-:36])[C:28]1=[O:37])([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>O1CCCC1>[Si:20]([N:27]1[CH:30]([CH2:31][CH:32]([OH:33])[CH2:2][C:1]([O:4][CH2:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:3])[CH:29]([N:34]=[N+:35]=[N-:36])[C:28]1=[O:37])([C:23]([CH3:25])([CH3:26])[CH3:24])([CH3:22])[CH3:21]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 8785Benzyl acetateHCID 2724682Lithium diisopropylamideHCID 20563653N-(t-butyldimethylsilyl)-3-azido-4-(2-oxoethyl)azetidin-2-one

生成物 1

HCID 20563667N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl 2-hydroxypropyl)-azetidin-2-one

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

反応条件

温度
-78 °C

実験手順

A solution of benzyl acetate (0.011 mol) in anhydrous tetrahydrofuran (5 ml) is added dropwise to solution of lithium diisopropylamide (0.011 mol) in anhydrous tetrahydrofuran (20 ml) at -78° C. After stirring 15 more min at -78° C. the reaction mixture is treated dropwise with a solution of N-(t-butyldimethylsilyl)-3-azido-4-(2-oxoethyl)-azetidin-2-one (0.01 mol) in tetrahydrofuran (10 ml). The mixture is stirred at -78° an additional 15 min and then quenched with 2.5 N hydrochloric acid (10 ml). The mixture is diluted with ethyl acetate, washed with water, 5% sodium bicarbonate solution, and brine, dried with magnesium sulfate, and evaporated under vacuum to afford N-(t-butyldimethylsilyl)-3-azido-4-(3-benzyloxycarbonyl 2-hydroxypropyl)-azetidin-2-one.

後処理

  1. stirringThe mixture is stirred at -78° an additional 15 min
  2. customquenched with 2.5 N hydrochloric acid (10 ml)
  3. additionThe mixture is diluted with ethyl acetate
  4. washwashed with water, 5% sodium bicarbonate solution, and brine
  5. dry with materialdried with magnesium sulfate
  6. customevaporated under vacuum

出典と根拠

ORDレコード
ord-9b44d0b96c4845fd9bec6323e0ba3501
出典データセット
uspto-grants-1981_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04298741

反応ノート

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