tert-Butyl [({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]acetate → tert-Butyl [({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]acetate

HRID 2400653Notes

Reaction equation

HRID 2400653 reaction equation
[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][NH:9][C:10]([C@@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][N:13]1[C:14](=[O:28])[N:15]2[O:20]CC1C=CC=CC=1)=[O:11])([CH3:4])([CH3:3])[CH3:2].[H][H]>CO.[Pd]>[C:1]([O:5][C:6](=[O:29])[CH2:7][O:8][NH:9][C:10]([C@@H:12]1[CH2:18][CH2:17][C@@H:16]2[CH2:19][N:13]1[C:14](=[O:28])[N:15]2[OH:20])=[O:11])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 86699610tert-Butyl [({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]acetateHCID 178418361HCID 178418361, compound

Product 1

HCID 86699611tert-Butyl [({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]acetateYield 89.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of tert-butyl[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]acetate 89 (0.23 g, 0.57 mml) in methanol (20 mL) was added 5% Pd/C (0.30 g). The mixture was hydrogenated under 35 psi hydrogen atmosphere at room temperature for 1 h. The catalyst was filtered out through Celite, and the filtrate was evaporated to give tert-butyl[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]acetate 90 (0.16 g. 89%) as a clear thick oil.

Workup

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

Sources & evidence

ORD record
ord-10b0849d4da54dfe97c05675f372937c
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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