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

HRID 451311Notes

Reaction equation

HRID 451311 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]([N:27]([CH3:29])[CH3:28])[CH:22]=1)=[O:19])C1C=CC=CC=1>[Pd].CO>[CH3:28][N:27]([CH3:29])[C:23]1[CH:22]=[C:21]([NH:20][C:18]([C@@H:13]2[CH2:12][CH2:11][C@@H:10]3[CH2:17][N:14]2[C:15](=[O:16])[N:9]3[OH:8])=[O:19])[CH:26]=[CH:25][N:24]=1

Participants

4

Reactant 1

HCID 58530144(2S,5R)-6-(Benzyloxy)-N-[2-(dimethylamino)pyridin-4-yl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 58530063(2S,5R)-N-[2-(dimethylamino)pyridin-4-yl]-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Palladium on carbon (10.4 mg; 10% Pd/C) was added to a solution of (2S,5R)-6-(benzyloxy)-N-[2-(dimethylamino)pyridin-4-yl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide (47.8 mg, 0.121 mmol) in methanol (2 mL) and the resulting mixture was stirred under hydrogen (balloon) overnight. HPLC analysis showed reaction complete. The reaction mixture was filtered through a microfilter and the filtrate was concentrated under vacuum to afford the title compound as a colorless oil which was used in the next step without further purification.

Workup

  1. customreaction complete
  2. filtrationThe reaction mixture was filtered through a microfilter
  3. concentrationthe filtrate was concentrated under vacuum

Sources & evidence

ORD record
ord-3fc75c5ef5574186835ccb22904c6ac4
Source dataset
uspto-grants-2013_07
Patent number
US08487093B2

Reaction notes

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