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

HRID 1053462Notes

Reaction equation

HRID 1053462 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][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[O:27])=[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][N:21]1[CH2:26][CH2:25][CH2:24][CH2:23][C:22]1=[O:27])=[O:19]

Participants

4

Reactant 1

HCID 86694076(2S,5R)-6-(benzyloxy)-7-oxo-N-(2-oxopiperidin-1-yl)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide

Product 1

HCID 86694077(2S,5R)-6-hydroxy-7-oxo-N-(2-oxopiperidin-1-yl)-1,6-diazabicyclo[3.2.1]octane-2-carboxamideYield 88.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of compound 257 (55 mg, 0.148 mmol) in 10 mL of MeOH was added 100 mg of Pd/C (10%, wet). The mixture was hydrogenated at room temperature for 2 h. The catalyst was removed by filtration through Celite pad. The filtrate was concentrated to afford compound 258 as a colorless gum (37 mg, 88%).

Workup

  1. customThe catalyst was removed by filtration through Celite pad
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-62c621271b5b4c44bbe806308d2e3371
Source dataset
uspto-grants-2016_07
Patent number
US09393239B2

Reaction notes

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