(2R,5S)-6-(benzyloxy)-N'-[(dimethylamino)acetyl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide → (2R,5S)-N'-[(dimethylamino)acetyl]-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide

HRID 1053454Notes

Reaction equation

HRID 1053454 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][NH:21][C:22](=[O:27])[CH2:23][N:24]([CH3:26])[CH3:25])=[O:19])C1C=CC=CC=1.[H][H]>CO.[Pd]>[CH3:26][N:24]([CH2:23][C:22]([NH:21][NH:20][C:18]([C@H:13]1[CH2:12][CH2:11][C@H:10]2[CH2:17][N:14]1[C:15](=[O:16])[N:9]2[OH:8])=[O:19])=[O:27])[CH3:25]

Participants

5

Reactant 2

HCID 86694068(2R,5S)-6-(benzyloxy)-N'-[(dimethylamino)acetyl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideHCID 178418361HCID 178418361, compound

Product 1

HCID 86694069(2R,5S)-N'-[(dimethylamino)acetyl]-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideYield 88%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,5S)-6-(benzyloxy)-N′-[(dimethylamino)acetyl]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 241 (0.15 g, 0.40 mml) in methanol (20 mL) was added 5% Pd/C (0.20 g). The mixture was hydrogenated under 10 psi hydrogen atmosphere at room temperature for 1 h. The catalyst was filtered out through Celite and the filtrate was evaporated to give (2R,5S)-N′-[(dimethylamino)acetyl]-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 242 (0.10 g, 88%) as a white foam.

Workup

  1. filtrationThe catalyst was filtered out through Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-d30c8547301b4be8bcd3d661ca048b55
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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