HCID 86700997, compound → HCID 86700998, compound

HRID 1427619Notes

Reaction equation

HRID 1427619 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]1[O:19][CH:20]=[N:21][N:22]=1)C1C=CC=CC=1>C1COCC1.[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]1[O:19][CH:20]=[N:21][N:22]=1

Participants

4

Reactant 1

HCID 86700997HCID 86700997, compound

Product 1

HCID 86700998HCID 86700998, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-6-(benzyloxy)-2-(1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (4.6 g, 15.3 mmol) in THF (150 mL) was added 10% Pd/C (1 g). The mixture was stirred under H2 atmosphere at rt for 3 hrs. The reaction mixture was then filtered and concentrated to afford (2S,5R)-6-hydroxy-2-(1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (2.9 g, 91%), which was used directly in the next step. ESI-MS (EI+, m/z): 211.1 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-d83e1a2793aa499cb3e17defb7d332b8
Source dataset
uspto-grants-2015_01
Patent number
US08933233B2

Reaction notes

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