Di-tert-butyl [{4-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]piperidin-1-yl}methylylidene]biscarbamate → Di-tert-butyl [{4-[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]piperidin-1-yl}methylylidene]biscarbamate

HRID 2400639Notes

Reaction equation

HRID 2400639 reaction equation
[C:1]([O:5][C:6](=[O:44])[NH:7][C:8]([N:17]1[CH2:22][CH2:21][CH:20]([O:23][NH:24][C:25]([C@@H:27]2[CH2:33][CH2:32][C@@H:31]3[CH2:34][N:28]2[C:29](=[O:43])[N:30]3[O:35]CC2C=CC=CC=2)=[O:26])[CH2:19][CH2:18]1)=[N:9][C:10](=[O:16])[O:11][C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:12]([O:11][C:10](=[O:16])[NH:9][C:8]([N:17]1[CH2:18][CH2:19][CH:20]([O:23][NH:24][C:25]([C@@H:27]2[CH2:33][CH2:32][C@@H:31]3[CH2:34][N:28]2[C:29](=[O:43])[N:30]3[OH:35])=[O:26])[CH2:21][CH2:22]1)=[N:7][C:6](=[O:44])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2])([CH3:13])([CH3:14])[CH3:15]

Participants

4

Reactant 1

HCID 86699596Di-tert-butyl [{4-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]piperidin-1-yl}methylylidene]biscarbamate

Product 1

HCID 86699597Di-tert-butyl [{4-[({[(2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]piperidin-1-yl}methylylidene]biscarbamateYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of di-tert-butyl[{4-[({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]oct-2-yl]carbonyl}amino)oxy]piperidin-1-yl}methylylidene]biscarbamate 66 (0.26 g, 0.42 mmol) and Pd/C (0.080 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 67 (0.21 g, 98%) as a white solid.

Workup

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

Sources & evidence

ORD record
ord-f1989a449f4a4d4799b24d0fd713fc3d
Source dataset
uspto-grants-2014_08
Patent number
US08796257B2

Reaction notes

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