3-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-benzoic acid ethyl ester → 4-(5-Ethoxycarbonylmethyl-pyridin-3-yl)-3-ethylaminomethyl-benzoic acid

HRID 554587Notes

Reaction equation

HRID 554587 reaction equation
C([O:3][C:4](=[O:37])[C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[N:13][CH:14]=[C:15]([CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:16]=2)=[C:7]([CH2:23][N:24](C(OCC2C=CC=CC=2)=O)[CH2:25][CH3:26])[CH:6]=1)C>CO>[CH2:21]([O:20][C:18]([CH2:17][C:15]1[CH:16]=[C:11]([C:8]2[CH:9]=[CH:10][C:5]([C:4]([OH:37])=[O:3])=[CH:6][C:7]=2[CH2:23][NH:24][CH2:25][CH3:26])[CH:12]=[N:13][CH:14]=1)=[O:19])[CH3:22]

Participants

3

Reactant 1

HCID 585652203-[(N-benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-benzoic acid ethyl ester

Product 1

HCID 585650534-(5-Ethoxycarbonylmethyl-pyridin-3-yl)-3-ethylaminomethyl-benzoic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-[(N-Benzyloxycarbonyl-N-ethyl-amino)-methyl]-4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-benzoic acid ethyl ester (0.5 g, 1 mmol) was dissolved in MeOH (20 mL), and the solution was purged with N2 for 10 minutes. 10% Palladium on carbon (0.2 g) was added, and the reaction was stirred under an atmosphere on H2 at room temperature for 3 hours. Additional 10% palladium on carbon (0.1 g) was added, and the reaction was stirred under H2 overnight. The mixture was purged with N2 and filtered over Celite. After washing with MeOH, the filtrate was concentrated to give 4-(5-ethoxycarbonylmethyl-pyridin-3-yl)-3-ethylaminomethyl-benzoic acid.

Workup

  1. customthe solution was purged with N2 for 10 minutes
  2. addition10% Palladium on carbon (0.2 g) was added
  3. additionAdditional 10% palladium on carbon (0.1 g) was added
  4. stirringthe reaction was stirred under H2 overnight
  5. customThe mixture was purged with N2
  6. filtrationfiltered over Celite
  7. washAfter washing with MeOH
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-53d8d3b57c764229af19bfe505b3cf2c
Source dataset
uspto-grants-2011_11
Patent number
US08049015B2

Reaction notes

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