HCID 86701381, compound → HCID 86701383, compound

HRID 870833Notes

Reaction equation

HRID 870833 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][C:20]([CH3:23])=[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][C:20]([CH3:23])=[N:21][N:22]=1

Participants

4

Reactant 1

HCID 86701381HCID 86701381, compound

Product 1

HCID 86701383HCID 86701383, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ((2S,5R)-6-(benzyloxy)-2-(5-methyl-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (0.2 g, 0.6 mmol) and 10% Pd/C (0.2 g) in THF (20 mL) 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-(5-methyl-1,3,4-oxadiazol-2-yl)-1,6-diazabicyclo[3.2.1]octan-7-one (0.13 g, 92%) as a white solid, which was used directly in the next step. ESI-MS (EI+, m/z): 225 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-88f61cb4f7ce4b209be6f8654544d1bd
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

Loading…