HCID 86701388, compound → HCID 86701389, compound

HRID 870845Notes

Reaction equation

HRID 870845 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]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[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]([N:23]2[CH2:28][CH2:27][N:26]([CH3:29])[CH2:25][CH2:24]2)=[N:21][N:22]=1

Participants

4

Reactant 1

HCID 86701388HCID 86701388, compound

Product 1

HCID 86701389HCID 86701389, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-6-(benzyloxy)-2-(5-(4-methylpiperazin-1-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (202 mg, 0.51 mmol) in THF (150 mL) was added 10% Pd/C (300 mg). The mixture was stirred under H2 atmosphere at rt for 3 hrs then filtered and concentrated to afford (2S,5R)-6-hydroxy-2-(5-(4-methylpiperazin-1-yl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (154 mg, 98%), which was used directly in the next step. ESI-MS (EI+, m/z): 309.1 [M+H]+.

Workup

  1. filtrationthen filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-05666172e7df4bed84b274dae4ac0edf
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

Loading…