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

HRID 851384노트

반응식

HRID 851384 반응식
[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]

참가 물질

5

반응물 2

HCID 6410tert-Butyl hydroperoxide2회HCID 53904921benzyl 4-[(2RS)-1-(tert-butyldimethylsilyl)-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
55 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ffaf633080cd4bae8aac0d6761627650
출처 데이터셋
uspto-grants-1983_05
특허 번호
US04383945

반응 노트

불러오는 중…