Acetic Anhydride → HCID 22449501, compound

HRID 355961Notes

Reaction equation

HRID 355961 reaction equation
[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]2[C:6]=1[C:7](=[O:19])[CH2:8][CH2:9][N:10]2[CH2:16][C:17]#[N:18])(=[O:3])[CH3:2].C(OC(=O)C)(=O)C>[Ni].C(O)(=O)C>[C:1]([NH:4][C:5]1[CH:14]=[CH:13][C:12]([CH3:15])=[C:11]2[C:6]=1[C:7](=[O:19])[CH2:8][CH2:9][N:10]2[CH2:16][CH2:17][NH2:18])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 22449545HCID 22449545, compound

Product 1

HCID 22449501HCID 22449501, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 176Acetic AcidSolvent

Procedure

The compound prepared in (2) above (650 mg) was dissolved into a mixed solvent of 10 ml of acetic acid and 30 ml of acetic anhydride. The mixture was catalytically hydrogenated with the addition of 2 ml of Raney nickel. After removing the catalyst by filtration, the reaction mixture was concentrated and chloroform was added to the residue, which was washed with saturated aqueous solution of sodium bicarbonate and saturated brine, and dried over anhydrous sodium sulfate. After evaporating the solvent, the residue was recrystallized from chloroform and ether to obtain 510 mg of the title compound.

Workup

  1. customAfter removing the catalyst
  2. filtrationby filtration
  3. concentrationthe reaction mixture was concentrated
  4. additionchloroform was added to the residue, which
  5. washwas washed with saturated aqueous solution of sodium bicarbonate and saturated brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. customAfter evaporating the solvent
  8. customthe residue was recrystallized from chloroform and ether

Sources & evidence

ORD record
ord-2d197e9f824e4871b4c9e902930f2eca
Source dataset
uspto-grants-1998_11
Patent number
US05834476

Reaction notes

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