(2R,5S)-6-(benzyloxy)-N'-methyl-7-oxo-N'-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide → HCID 86694060, compound

HRID 1053444Notes

Reaction equation

HRID 1053444 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][N:21]([CH3:26])[C:22](=[O:25])[CH2:23][CH3:24])=[O:19])C1C=CC=CC=1.[H][H]>CO.[Pd]>[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][N:21]([CH3:26])[C:22](=[O:25])[CH2:23][CH3:24])=[O:19]

Participants

5

Reactant 2

HCID 86694059(2R,5S)-6-(benzyloxy)-N'-methyl-7-oxo-N'-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideHCID 178418361HCID 178418361, compound

Product 1

HCID 86694060HCID 86694060, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,5S)-6-(benzyloxy)-N′-methyl-7-oxo-N′-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 226 (0.19 g, 0.52 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 through Celite, and the filtrate was evaporated to give (2R,5S)-6-hydroxy-N′-methyl-7-oxo-N′-propanoyl-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 227 (0.11 g, 79%) as a brown foam.

Workup

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

Sources & evidence

ORD record
ord-5c3a21dee246463bae5619e8973067f7
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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