1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → HCID 22591861, compound

HRID 22896Notes

Reaction equation

HRID 22896 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[CH2:14][CH:13]([C:17]([OH:19])=O)[CH2:12]1.[NH2:20][C:21]1([CH:27](C)[C:28]([O:30][CH2:31][CH3:32])=[O:29])C=CC=NC1.[CH:34]1[CH:39]=[N:38][C:37]2N(O)N=N[C:36]=2[CH:35]=1.CCN(C(C)C)C(C)C.CCN=C=NCCCN(C)C>CN(C=O)C.CCOC(C)=O>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:15](=[O:16])[CH2:14][CH:13]([C:17]([NH:20][CH:21]([C:36]2[CH:37]=[N:38][CH:39]=[CH:34][CH:35]=2)[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:19])[CH2:12]1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 81531DiisopropylethylamineHCID 181649HOAtHCID 225917921-(2-Methyl-5-nitrophenyl)-5-oxo-3-pyrrolidinecarboxylic acidHCID 69749277Ethyl 3-amino-3-pyridylpropanoate

Product 1

HCID 22591861HCID 22591861, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 1-(2-methyl-5-nitrophenyl)-5-oxopyrrolidine-3-carboxylic acid (5 g), ethyl 3-amino-3-pyridylpropanoate and HOAt in DMF at 0° C. was added i-Pr2NEt, followed by EDCI, in portions. The reaction mixture was then warmed up to room temperature and stirred overnight. The reaction solution was diluted with EtOAc 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 chromatography with 10% MeOH/EtOAc as eluent. A 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 chromatography with 10% MeOH/EtOAc as eluent
  5. customA yellow solid was obtained

Sources & evidence

ORD record
ord-b8a77246e2444f54bbfe9a4149ed6988
Source dataset
uspto-grants-2005_02
Patent number
US06849639B2

Reaction notes

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