Cornforth reagent → 4-Acetyl-3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazole

HRID 612899Notes

Reaction equation

HRID 612899 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([CH:17]([OH:19])[CH3:18])=[C:15]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[Cr](O[Cr]([O-])(=O)=O)([O-])(=O)=O.[NH+]1C=CC=CC=1.[NH+]1C=CC=CC=1>C(Cl)Cl>[C:17]([C:16]1[C:12]([O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[N:13][O:14][C:15]=1[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)(=[O:19])[CH3:18]

Participants

4

Reactant 2

HCID 2724130Cornforth reagentHCID 195966673-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-(1-hydroxyethyl)-5-phenylisoxazole

Product 1

HCID 195966344-Acetyl-3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-phenylisoxazoleYield 87.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-(1-hydroxyethyl)-5-phenylisoxazole (0.3 g) was dissolved in methylene chloride (3 ml), and pyridinium dichromate (0.49 g) was added thereto at room temperature, followed by stirring of the resulting mixture at the same temperature for 24 hours. After the reaction, insolubles were filtered and the solvent of the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1) to obtain the title compound (0.26 g, 87%) as a colorless powder.

Workup

  1. customat room temperature
  2. customAfter the reaction, insolubles
  3. filtrationwere filtered
  4. customthe solvent of the filtrate was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=2/1)

Sources & evidence

ORD record
ord-ad86c60b486f4b5fb82618657c4a6a3c
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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