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

HRID 1719286

반응식

HRID 1719286 반응식
[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]

참가 물질

5

반응물 2

HCID 6410tert-Butyl hydroperoxide2회HCID 53759236benzyl 4-[(2RS)-4-oxoazetidin-2-yl]but-2-enoate

생성물 1

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

시약·촉매·용매 2

HCID 178479786HCID 178479786, 화합물촉매2회HCID 176Acetic Acid용매

반응 조건

온도
50 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-f87ea710f6b24e959a9829b34b7ae78b
출처 데이터셋
uspto-grants-1985_09
특허 번호
US04539152

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