(2S,5R)-N-(2-Amino-2-oxoethoxy)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide → (2S,5R)-N-(2-Amino-2-oxoethoxy)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

HRID 2400632Notes

Reaction equation

HRID 2400632 reaction equation
[NH2:1][C:2](=[O:25])[CH2:3][O:4][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]>CO.[Pd]>[NH2:1][C:2](=[O:25])[CH2:3][O:4][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]

Participants

4

Reactant 1

HCID 86693952(2S,5R)-N-(2-Amino-2-oxoethoxy)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 86693953(2S,5R)-N-(2-Amino-2-oxoethoxy)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamideYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of (2S,5R)—N-(2-amino-2-oxoethoxy)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 54 (0.11 g, 0.40 mmol) and Pd/C (0.040 g) in methanol (10 mL) was hydrogenated at 1 atm at room temperature for 3 h. The mixture was filtered through Celite pad and concentrated to provide 55 (0.10 g, 98%) as a white solid.

Workup

  1. filtrationThe mixture was filtered through Celite pad
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-6946510e7a85477f812c2805e93b9f8f
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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