(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide → Avibactam Impurity 10

HRID 925145Notes

Reaction equation

HRID 925145 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]([NH2:20])=[O:19])C1C=CC=CC=1>CO.[C].[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]([NH2:20])=[O:19]

Participants

4

Reactant 1

HCID 57389435(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 66921332Avibactam Impurity 10Yield 119.3%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

445 mg of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide was dissolved in methanol (16 mL), and 80 mg of 10% palladium-carbon (50% water content) was added, followed by stifling for 0.75 hours under hydrogen atmosphere. The catalyst of the reaction mixture was filtered through celite, and the solvent was concentrated under reduced pressure and dried under vacuum to afford 357 mg of the title compound as a colorless solid (quantitative).

Workup

  1. filtrationThe catalyst of the reaction mixture was filtered through celite
  2. concentrationthe solvent was concentrated under reduced pressure
  3. customdried under vacuum

Sources & evidence

ORD record
ord-2a8a4cfa32ea437abe75d5579fb2c676
Source dataset
uspto-grants-2016_03
Patent number
US09284273B2

Reaction notes

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