HCID 86701013, compound → HCID 86701014, compound

HRID 1855173Notes

Reaction equation

HRID 1855173 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:22][C:21]([C:23]([NH2:25])=[O:24])=[N:20][N:19]=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:22][C:21]([C:23]([NH2:25])=[O:24])=[N:20][N:19]=1

Participants

4

Reactant 1

HCID 86701013HCID 86701013, compound

Product 1

HCID 86701014HCID 86701014, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazole-2-carboxamide (0.14 g, 0.41 mmol) in THF (10 mL) was added 10% Pd/C (0.14 g). The mixture was stirred under H2 atmosphere at rt for 3 hrs then filtered and concentrated to provide 5-((2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazole-2-carboxamide (103 mg, 100%), which was directly used in the next step. ESI-MS (EI+, m/z): 254 [M+H]+.

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-1a3c03addc54429f8a2f12604e9ade93
Source dataset
uspto-grants-2015_02
Patent number
US08962843B2

Reaction notes

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