Benzyl Bromide → 5-(4-Benzyloxyphenyl)-3-(2-(N-tert-butoxycarbonylamino)ethoxy)isoxazole

HRID 612907Notes

Reaction equation

HRID 612907 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][O:11][C:12]1[CH:16]=[C:15]([C:17]2[CH:22]=[CH:21][C:20]([OH:23])=[CH:19][CH:18]=2)[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[CH2:26](Br)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>CN(C)C=O>[CH2:26]([O:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]2[O:14][N:13]=[C:12]([O:11][CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH:16]=2)=[CH:22][CH:21]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 135624007HCID 135624007, compound

Product 1

HCID 195964525-(4-Benzyloxyphenyl)-3-(2-(N-tert-butoxycarbonylamino)ethoxy)isoxazoleYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-(N-tert-Butoxycarbonylamino)ethoxy)-5-(4-hydroxyphenyl)isoxazole (0.2 g) was dissolved in dimethylformamide (2 ml), and 55% sodium hydride (oil, 0.03 g) was added thereto at 5° C. under a nitrogen atmosphere, followed by stirring of the resulting mixture at the same temperature for 10 minutes. Then, benzyl bromide (0.08 ml) was added dropwise thereto and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into 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 (0.14 g, 54%) as a colorless powder.

Workup

  1. customat 5° C.
  2. stirringthe mixture was stirred at room temperature for 30 minutes
  3. additionThe reaction mixture was poured into ice-cold water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous NaCl solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. filtrationAfter filtration
  8. customthe solvent was evaporated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=3/1)

Sources & evidence

ORD record
ord-6a100895d16f497b893dc63bcdfb0540
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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