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

HRID 1719286

反応式

HRID 1719286 の反応式
[O:1]=[C:2]1[NH:5][CH:4]([CH2:6][CH:7]=[CH:8][C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:3]1.C([O:23]O)(C)(C)C>C(O)(=O)C.[Na+].[Na+].Cl[Pd+2](Cl)(Cl)Cl>[O:23]=[C:7]([CH2:6][CH:4]1[CH2:3][C:2](=[O:1])[NH:5]1)[CH2:8][C:9]([O:11][CH2:12][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:10]

参加物

5

反応物 2

HCID 6410tert-Butyl hydroperoxide2 回HCID 53759236benzyl 4-[(2RS)-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
50 °C

実験手順

A mixture of benzyl 4-[(2RS)-4-oxoazetidin-2-yl]-but-2-enoate (167 mg), tert-butylhydroperoxide (0.3 ml), and sodium tetrachloropalladate (80 mg) in 67% aqueous acetic acid (2.7 ml) was heated at 50° C. for 8.5 hours. Additional tert-butylhydroperoxide (0.5 ml) and sodium tetrachloropalladate (40 mg) were added. The reaction mixture was stirred at room temperature for three days and heated at 50° C. for 14 hours. After evaporation of the solvent in vacuo, the residue was taken up into ethyl acetate (20 ml) and washed with dilute aqueous sodium chloride. Drying over magnesium sulfate and evaporation left an oil (200 mg), which was chromatographed on silica gel plate (developing solvent: 20% acetone in dichloromethane) afforded benzyl 3-oxo-4-[(2RS)-4-oxoazetidin-2-yl]butanoate (66 mg).

後処理

  1. temperatureheated at 50° C. for 14 hours
  2. customAfter evaporation of the solvent in vacuo
  3. washwashed with dilute aqueous sodium chloride
  4. dry with materialDrying over magnesium sulfate and evaporation
  5. waitleft an oil (200 mg), which
  6. customwas chromatographed on silica gel plate (developing solvent: 20% acetone in dichloromethane)

出典と根拠

ORDレコード
ord-f87ea710f6b24e959a9829b34b7ae78b
出典データセット
uspto-grants-1985_09
特許番号
US04539152

関連ノート

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