Acetic Acid → Ethyl 3-{(1-(3-aminophenyl)-5-oxopyrrolidin-3-yl)carbonylamino}-3-(3-pyridyl)propanoate

HRID 22895

Reaction equation

HRID 22895 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([NH:18][CH:19]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-])=O.CC(O)=O>C1COCC1.CO.O.[Zn]>[NH2:1][C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([NH:18][CH:19]([C:26]3[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=3)[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22])=[O:17])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 22591756Ethyl 3-{(1-(3-nitrophenyl)-5-oxopyrrolidin-3-yl) carbonylamino}-3-(3-pyridyl)propanoate

Product 1

HCID 10200775Ethyl 3-{(1-(3-aminophenyl)-5-oxopyrrolidin-3-yl)carbonylamino}-3-(3-pyridyl)propanoate

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 21892291Methanol tetrahydrofuran waterSolvent

Procedure

Ethyl 3-{(1-(3-nitrophenyl)-5-oxopyrrolidin-3-yl)carbonylamino}-3-(3-pyridyl)propanoate was dissolved in THF/MeOH/H2O solution at 0° C. AcOH was added followed by activated Zn powder. The reaction was then stirred at room temperature for 5 hours. The Zn powder was filtered through a pad of celite. The filtrate was concentrated in vacuo and the residue was re-dissolved in EtOAc. A white precipitate formed and was removed by filtration. The organic solution was concentrated in vacuo to afforded yellow foam. MS (ES+): 397.0 (M+H)+.

Workup

  1. filtrationThe Zn powder was filtered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. dissolutionthe residue was re-dissolved in EtOAc
  4. customA white precipitate formed
  5. customwas removed by filtration
  6. concentrationThe organic solution was concentrated in vacuo
  7. customto afforded yellow foam

Sources & evidence

ORD record
ord-e12380c8349b4d6cb255b86ce00751ee
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Linked notes

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