Acetic Anhydride → HCID 53649372, compound

HRID 979815Notes

Reaction equation

HRID 979815 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:11](=O)[CH2:12][CH2:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH:5]=[CH:6][C:7]=1[N+:8]([O-])=O.[C:20](OC(=O)C)(=[O:22])[CH3:21]>C(OCC)(=O)C.[Pd]>[CH2:17]([O:16][C:14](=[O:15])[CH2:13][CH2:12][CH2:11][C:4]1[CH:5]=[CH:6][C:7]([NH:8][C:20](=[O:22])[CH3:21])=[C:2]([CH3:1])[CH:3]=1)[CH3:18]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 86741184HCID 86741184, compound

Product 1

HCID 53649372HCID 53649372, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

The product from Example 101 (18.05 g) was dissolved in ethyl acetate (1 L) and subjected to hydrogenation with 20% Pd/C (dry) in the presence of acetic anhydride (15 ml). The reaction mixture was filtered, and the solvent was evaporated. The residue was dissolved in ethanol (250 ml) and a catalytic amount of sulfuric acid (5 drops) was added. The resulting solution was hydrogenated at room temperature overnight. The catalyst was filtered and the filtrate was washed with 5% sodium bicarbonate dried and the solvent was evaporated to afford the desired compound in 90% yield.

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe solvent was evaporated
  3. dissolutionThe residue was dissolved in ethanol (250 ml)
  4. additiona catalytic amount of sulfuric acid (5 drops) was added
  5. filtrationThe catalyst was filtered
  6. washthe filtrate was washed with 5% sodium bicarbonate
  7. customdried
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-14be61d078e74eb590f30834d549c129
Source dataset
uspto-grants-1987_01
Patent number
US04634705

Reaction notes

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