tert-Butyl hydroperoxide → 4-(3-Benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

HRID 851384ノート

反応式

HRID 851384 の反応式
[Si]([N:8]1[C:11](=[O:12])[CH2:10][CH:9]1[CH2:13][CH:14]=[CH:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17])(C(C)(C)C)(C)C.C([O:30]O)(C)(C)C>C(O)(=O)C.[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl>[O:30]=[C:14]([CH2:13][CH:9]1[CH2:10][C:11](=[O:12])[NH:8]1)[CH2:15][C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]

参加物

5

反応物 2

HCID 6410tert-Butyl hydroperoxide2 回HCID 53904921benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate

生成物 1

HCID 127954624-(3-Benzyloxycarbonyl-2-oxopropyl)-azetidin-2-one

試薬・触媒・溶媒 2

HCID 178479786HCID 178479786、化合物触媒2 回HCID 176Acetic Acid溶媒

反応条件

温度
55 °C

実験手順

To a solution of benzyl 4-[(2RS)-1-(tert-butyl-dimethylsilyl)-4-oxoazetidin-2-yl]but-2-enoate (50 mg) in 60% aqueous acetic acid (1.5 ml) were added tert-butyl-hydroperoxide (40 μl) and sodium tetrachloropalladate (18 mg). The solution was heated at 55° C. for 5.5 hours. Additional tert-butyl-hydroperoxide (100 μl) and sodium tetrachloropalladate (18 mg) were added and stirring at 50° C. was continued for further 11 hours. After evaporation of the solvent in vacuo, the residue was taken up into ethyl acetate and washed in turn with water (twice) and brine. Drying over magnesium sulfate and removal of the solvent left an oil (30 mg) which was chromatographed on a silica gel plate (developing solvent: 25% acetone in benzene) afforded benzyl 3-oxo-4-[(2RS)-4-oxoazetidin-2-yl]butanoate (13 mg).

後処理

  1. customAfter evaporation of the solvent in vacuo
  2. washwashed in turn with water (twice) and brine
  3. dry with materialDrying over magnesium sulfate and removal of the solvent
  4. waitleft an oil (30 mg) which
  5. customwas chromatographed on a silica gel plate (developing solvent: 25% acetone in benzene)

出典と根拠

ORDレコード
ord-ffaf633080cd4bae8aac0d6761627650
出典データセット
uspto-grants-1983_05
特許番号
US04383945

反応ノート

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