HCID 86693977, compound → (2S,5R)-6-hydroxy-N-[(1-methyl-1H-imidazol-5-yl)methoxy]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 330953Notes

Reaction equation

HRID 330953 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][O:21][CH2:22][C:23]1[N:27]([CH3:28])[CH:26]=[N:25][CH:24]=1)=[O:19])C1C=CC=CC=1>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][O:21][CH2:22][C:23]1[N:27]([CH3:28])[CH:26]=[N:25][CH:24]=1)=[O:19]

Participants

4

Reactant 1

HCID 86693977HCID 86693977, compound

Product 1

HCID 86693978(2S,5R)-6-hydroxy-N-[(1-methyl-1H-imidazol-5-yl)methoxy]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamideYield 79%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S,5R)-6-(benzyloxy)-N-[(1-methyl-1H-imidazol-5-yl)methoxy]-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 101 (0.40 g, 0.90 mmol) and Pd/C (0.13 g) in methanol (20 mL) was hydrogenated at 1 atm at room temperature for 3 h. The mixture was filtered through Celite pad and concentrated to give a residue which was subjected to chromatography to give 102 (0.21 g, 75%) as a white foam.

Workup

  1. filtrationThe mixture was filtered through Celite pad
  2. concentrationconcentrated
  3. customto give a residue which

Sources & evidence

ORD record
ord-20bb454187b243d1a5f019b0686db3db
Source dataset
uspto-grants-2014_11
Patent number
US08877743B2

Reaction notes

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