3-(2-{6-methyl-2-oxo-3-(benzyloxycarbonylamino)-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester → 3-(2-{6-methyl-2-oxo-3-amino-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

HRID 1602665Notes

Reaction equation

HRID 1602665 reaction equation
[CH2:1]([O:3][C:4](=[O:36])[CH2:5][C@H:6]([NH:13][C:14](=[O:35])[CH2:15][N:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH:23]C(OCC2C=CC=CC=2)=O)[C:17]1=[O:34])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]>CCO.[Pd]>[CH2:1]([O:3][C:4](=[O:36])[CH2:5][C@H:6]([NH:13][C:14](=[O:35])[CH2:15][N:16]1[C:21]([CH3:22])=[CH:20][CH:19]=[C:18]([NH2:23])[C:17]1=[O:34])[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[CH3:2]

Participants

4

Reactant 1

HCID 540816963-(2-{6-methyl-2-oxo-3-(benzyloxycarbonylamino)-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

Product 1

HCID 540690173-(2-{6-methyl-2-oxo-3-amino-2H-pyridin-1-yl}-acetylamino)-3(S)-pyridin-3-yl-propionic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

##STR54## To a degassed solution of the pyridone 16-5 (243 mg; 0.49 mmol) in EtOH (20 mL) was added 10% Pd on carbon (25 mg) and this was then stirred under an atmosphere of hydrogen gas (balloon) for 3 hours. The mixture was filtered through a pad of celite and the solvent removed to give the title compound (16-6) as a viscous oil which was used as such in the next step.

Workup

  1. filtrationThe mixture was filtered through a pad of celite
  2. customthe solvent removed

Sources & evidence

ORD record
ord-c432d9b3cc3d4a0ba6fb89fee3ed9595
Source dataset
uspto-grants-1999_11
Patent number
US05981546

Reaction notes

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