Acetic Anhydride → HCID 12883705, compound

HRID 894318Notes

Reaction equation

HRID 894318 reaction equation
[C:1]([CH:3]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].[C:25](OC(=O)C)(=[O:27])[CH3:26]>[Ni].C(OCC)(=O)C>[C:25]([NH:2][CH2:1][CH:3]([C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH3:19])[CH:16]=2)[N:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1)[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:27])[CH3:26]

Participants

5

Reactant 2

HCID 7918Acetic AnhydrideHCID 10947487HCID 10947487, compound

Product 1

HCID 12883705HCID 12883705, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of Compound 1A, prepared above, (7.4 g, 0.022 mole) in 150 ml of acetic anhydride was hydrogenated for 20 hours at 50 psi, using about 10 g of Raney nickel as a catalyst. The catalyst was then removed by filtration, and the solvent was evaporated in vacuo to leave a thick syrup. This syrup was dissolved in 200 ml of ethyl acetate which was then washed five times with 6% aqueous potassium carbonate solution and dried over MgSO4. The solvent was then evaporated in vacuo, and the syrup which remained was crystallized from ethyl acetate:petroleum ether. One recrystallization from the same solvent pair yielded 4.6 g (56% theory) of product, mp. 88°-90° C.

Workup

  1. customThe catalyst was then removed by filtration
  2. customthe solvent was evaporated in vacuo
  3. customto leave a thick syrup
  4. washwas then washed five times with 6% aqueous potassium carbonate solution
  5. dry with materialdried over MgSO4
  6. customThe solvent was then evaporated in vacuo
  7. customthe syrup which remained was crystallized from ethyl acetate
  8. customOne recrystallization from the same solvent pair
  9. customyielded 4.6 g (56% theory) of product, mp. 88°-90° C.

Sources & evidence

ORD record
ord-53c2a0fe832d44b3993cc35214e2bdb3
Source dataset
uspto-grants-1981_08
Patent number
US04283410

Reaction notes

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