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

HRID 1755828Notes

Reaction equation

HRID 1755828 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-6c9ec01561794aa789802b107cbe8b03
Source dataset
uspto-grants-1995_08
Patent number
US05438118

Reaction notes

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