Ozone → N-benzyloxycarbonyl-N-(2-oxo-ethyl)-D-alanine t-butyl ester

HRID 1755828노트

반응식

HRID 1755828 반응식
[C:1]([O:5][C:6](=[O:23])[C@@H:7]([CH3:22])[N:8]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:9][CH:10]=C)([CH3:4])([CH3:3])[CH3:2].[O:24]=[O+][O-]>C(Cl)Cl>[C:1]([O:5][C:6](=[O:23])[C@@H:7]([CH3:22])[N:8]([C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:9][CH:10]=[O:24])([CH3:4])([CH3:3])[CH3:2]

참가 물질

4

반응물 2

HCID 24823OzoneHCID 54427579N-benzyloxycarbonyl-N-allyl-D-alanine t-butyl ester

생성물 1

HCID 53883224N-benzyloxycarbonyl-N-(2-oxo-ethyl)-D-alanine t-butyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Cbz-N-allyl-D-alanine t-butylester (70) in methylene chloride is treated with ozone at -78° C. until a blue color persists. The ozonide is quenched with dimethylsulfide and allowed to warm to room temperature. Excess dimethylsulfide is removed by bubbling a stream of nitrogen into the solution. After evaporation of solvent the product is purified by flash chromatography over silica gel to give (71).

후처리

  1. customThe ozonide is quenched with dimethylsulfide
  2. customExcess dimethylsulfide is removed
  3. customby bubbling a stream of nitrogen into the solution
  4. customAfter evaporation of solvent the product
  5. customis purified by flash chromatography over silica gel

출처 및 근거

ORD 기록
ord-6c9ec01561794aa789802b107cbe8b03
출처 데이터셋
uspto-grants-1995_08
특허 번호
US05438118

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