Methanol → HCID 19596442, compound

HRID 612876Notes

Reaction equation

HRID 612876 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17]([OH:19])=[O: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].[CH3:26]O>C1C=CC=CC=1.C[Si](C=[N+]=[N-])(C)C>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[C:16]([C:17]([O:19][CH3:26])=[O: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])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 887MethanolHCID 19596598HCID 19596598, compound

Product 1

HCID 19596442HCID 19596442, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 167693TrimethylsilyldiazomethaneSolvent

Procedure

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-4-carboxy-5-phenylisoxazole (0.2 g) was dissolved in a mixture of methanol and benzene (1:5, 10 ml), and trimethylsilyldiazomethane (0.6 ml, 2.0M hexane solution) was added dropwise thereto under ice-cooling, followed by stirring of the mixture at room temperature for 30 minutes. The reaction mixture was poured into an ice-cold water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution and dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1) to obtain the title compound (0.17 g, 81%) as a colorless solid.

Workup

  1. additionwas added dropwise
  2. temperatureunder ice-cooling
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous NaCl solution
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationAfter filtration
  7. customthe solvent was evaporated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-181ce0e321674430890f63f19c6d1f4a
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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