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

HRID 1755828ノート

反応式

HRID 1755828 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6c9ec01561794aa789802b107cbe8b03
出典データセット
uspto-grants-1995_08
特許番号
US05438118

反応ノート

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