Diisopropylethylamine → Ethyl 3-{(1-(3-nitrophenyl)-5-oxopyrrolidin-3-yl) carbonylamino}-3-(3-pyridyl)propanoate

HRID 22894Notes

Reaction equation

HRID 22894 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([OH:18])=O)[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[NH2:19][C:20]1([CH:26](C)[C:27]([O:29][CH2:30][CH3:31])=[O:28])C=CC=NC1.[CH:33]1[CH:38]=[N:37][C:36]2N(O)N=N[C:35]=2[CH:34]=1.CCN(C(C)C)C(C)C.Cl.CN(C)CCCN=C=NCC>CN(C=O)C.CCOC(C)=O>[N+:1]([C:4]1[CH:5]=[C:6]([N:10]2[C:14](=[O:15])[CH2:13][CH:12]([C:16]([NH:19][CH:20]([C:35]3[CH:36]=[N:37][CH:38]=[CH:33][CH:34]=3)[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:18])[CH2:11]2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

8

Reactant 5

HCID 81531DiisopropylethylamineHCID 181649HOAtHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27418301-(3-Nitrophenyl)-5-oxopyrrolidine-3-carboxylic acidHCID 69749277Ethyl 3-amino-3-pyridylpropanoate

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(3-nitrophenyl)-5-oxopyrrolidine-3-carboxylic acid (5 g, 0.02 mol), ethyl 3-amino-3-pyridylpropanoate (HCl salt) (0.03 mol) and HOAt (0.02 mol) in DMF (80 mL) at 0° C. was added i-Pr2NEt (0.03 mol), followed by 1-(3-dimethylaminopropyl)-3-ethyl carbodiimide hydrochloride (EDCI) (0.04 mol), in portions. The reaction mixture was then warmed up to room temperature and stirred overnight. The reaction solution was diluted with EtOAc (150 mL) and the organic phase was washed with saturated NaHCO3 and NaCl aqueous solution. The organic layer was dried over Na2SO4, concentrated in vacuo. The crude product was purified by flash column with 10% MeOH/EtOAc as eluent. Yellow solid was obtained. MS (ES+): 427.5 (M+H)+.

Workup

  1. washthe organic phase was washed with saturated NaHCO3 and NaCl aqueous solution
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product was purified by flash column with 10% MeOH/EtOAc as eluent
  5. customYellow solid was obtained

Sources & evidence

ORD record
ord-de130ab3e91e4f1ea1f49e82f91d958a
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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