2-(6-Amino-pyridin-3-ylmethyl)-N-benzyl-N-benzyloxy-succinamic acid → 2-(6-Amino-pyridin-3-ylmethyl)-N-benzyl-N-hydroxy-succinamic acid

HRID 29764Notes

Reaction equation

HRID 29764 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:13][C:14]([N:16]([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:17]CC2C=CC=CC=2)=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1>CO.[Pd]>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([CH2:13][C:14]([N:16]([CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[OH:17])=[O:15])[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 537218912-(6-Amino-pyridin-3-ylmethyl)-N-benzyl-N-benzyloxy-succinamic acid

Product 1

HCID 98404282-(6-Amino-pyridin-3-ylmethyl)-N-benzyl-N-hydroxy-succinamic acidYield 22%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-(6-Amino-pyridin-3-ylmethyl)-N-benzyl-N-benzyloxy-succinamic acid (0.9 g, 1.7 mmol) and palladium (0.5 g, 5% on charcoal) in methanol (100 mL) was hydrogenated at 1 bar for 2 h. The reaction mixture was filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CHCl3/MeOH/H2O, 10:5:1) to give the title compound (123 mg, 22%).

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by flash chromatography (CHCl3/MeOH/H2O, 10:5:1)

Sources & evidence

ORD record
ord-bbf0e600825442c5910a85d55cfa8c95
Source dataset
uspto-grants-2008_09
Patent number
US07423012B2

Reaction notes

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