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

HRID 1755828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1755828
[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]

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-6c9ec01561794aa789802b107cbe8b03
Quelldatensatz
uspto-grants-1995_08
Patentnummer
US05438118

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