(2S,5R)-6-(Benzyloxy)-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide → (2S,5R)-6-hydroxy-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 451309Notes

Reaction equation

HRID 451309 reaction equation
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[CH:22]=1)=[O:19])C1C=CC=CC=1>[Pd].CO>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[CH2:11][CH2:12][C@H:13]2[C:18]([NH:20][C:21]1[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[CH:22]=1)=[O:19]

Participants

4

Reactant 1

HCID 58530125(2S,5R)-6-(Benzyloxy)-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 58530037(2S,5R)-6-hydroxy-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (13.4 mg; 10% Pd/C) was added to a solution of (2S,5R)-6-(benzyloxy)-N-(2-methoxypyridin-4-yl)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (43.6 mg, 0.114 mmol) in methanol (1 mL) and the resulting mixture was stirred under hydrogen (balloon) overnight. HPLC analysis showed reaction complete. The reaction mixture was faltered through a microfilter and the filtrate was concentrated under vacuum to afford the title compound as an impure colorless oil.

Workup

  1. customreaction complete
  2. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-30b3ef07d86247068ead197e68bf4247
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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