HCID 15453983, compound → HCID 15453986, compound

HRID 1870293Notes

Reaction equation

HRID 1870293 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][S:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([N+:21]([O-])=O)[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C(O)(=O)C.[Zn]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][S:11][C:12]1[C:16]2[CH:17]=[CH:18][CH:19]=[C:20]([NH2:21])[C:15]=2[O:14][N:13]=1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 15453983HCID 15453983, compound

Product 1

HCID 15453986HCID 15453986, compoundYield 100.9%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

To a solution of 3-(2-(N-t-butoxycarbonylamino)ethylthio)-7-nitro-1,2-benzisoxazole (250 mg) in 90% aqueous acetic acid (2 ml) was added zinc powder (250 mg) with stirring under ice cooling, and the mixture was then stirred at room temperature for 30 minutes. After the completion of the reaction, the reaction mixture was filtered with Celite and the filtrate was concentrated under reduced pressure. Water was added to the residue, then extracted with ethyl acetate. The combined extracts were washed with brine and dried over anhydrous magnesium sulphate. After filtration, the solvent was evaporated under reduced pressure and the residue was purified by silical gel column chromatography with ethyl acetate as an eluent, to give the title compound (230 mg, quant).

Workup

  1. stirringthe mixture was then stirred at room temperature for 30 minutes
  2. customAfter the completion of the reaction
  3. filtrationthe reaction mixture was filtered with Celite
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. additionWater was added to the residue
  6. extractionextracted with ethyl acetate
  7. washThe combined extracts were washed with brine
  8. dry with materialdried over anhydrous magnesium sulphate
  9. filtrationAfter filtration
  10. customthe solvent was evaporated under reduced pressure
  11. customthe residue was purified by silical gel column chromatography with ethyl acetate as an eluent

Sources & evidence

ORD record
ord-4429085c34a74e7b810032958f054ee8
Source dataset
uspto-grants-2000_08
Patent number
US06096771

Reaction notes

Loading…