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

HRID 2400716Notes

Reaction equation

HRID 2400716 reaction equation
[C:1]([N:4]([CH3:25])[NH:5][C:6]([C@H:8]1[CH2:14][CH2:13][C@H:12]2[CH2:15][N:9]1[C:10](=[O:24])[N:11]2[O:16]CC1C=CC=CC=1)=[O:7])(=[O:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([N:4]([CH3:25])[NH:5][C:6]([C@H:8]1[CH2:14][CH2:13][C@H:12]2[CH2:15][N:9]1[C:10](=[O:24])[N:11]2[OH:16])=[O:7])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 86694050(2R,5S)-N'-acetyl-6-(benzyloxy)-N'-methyl-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideHCID 178418361HCID 178418361, compound

Product 1

HCID 86694051(2R,5S)-N'-acetyl-6-hydroxy-N'-methyl-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideYield 101.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of (2R,5S)—N′-acetyl-6-(benzyloxy)-N′-methyl-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 213 (0.20 g, 0.57 mml) in methanol (20 mL) was added 5% Pd/C (0.30 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′-acetyl-6-hydroxy-N′-methyl-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 214 (0.15 g, 99%) as a colorless foam.

Workup

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

Sources & evidence

ORD record
ord-f3534cc674fa4e49845be2e10bc1255a
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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