HCID 19596615, compound → HCID 19596640, compound

HRID 612902Notes

Reaction equation

HRID 612902 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]([N+:23]([O-])=O)=[CH:19][CH:18]=2)[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.O.[Zn]>[NH2:23][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])([CH3:3])[CH3:2])=[O:7])[CH:16]=2)=[CH:22][CH:21]=1

Participants

5

Reactant 1

HCID 19596615HCID 19596615, compound

Product 1

HCID 19596640HCID 19596640, compoundYield 90%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalyst2×HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

3-(2-(N-tert-butoxycarbonylamino)ethoxy)-5-(4-nitrophenyl)isoxazole (0.55 g) was dissolved in a mixture of acetic acid and water (9:1, 5.5 ml), and zinc powder (0.55 g) was added thereto at room temperature, followed by stirring of the resulting mixture at the same temperature for 2 hours. After the reaction, zinc powder was filtered off and the filtrate was 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=2/1) to obtain the title compound (0.45 g, 90%) as a colorless powder.

Workup

  1. additionwas added
  2. customat room temperature
  3. filtrationwas filtered off
  4. extractionthe filtrate was extracted 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=2/1)

Sources & evidence

ORD record
ord-849a7d4d42e4431a8e07eb645b9a2d62
Source dataset
uspto-grants-1999_12
Patent number
US06005116

Reaction notes

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