HCID 86701392, compound → HCID 86701394, compound

HRID 870849Notes

Reaction equation

HRID 870849 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][O:26][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[CH2:24][CH2:25][O:26][CH2:27][CH2:28]2)=[N:21][N:22]=1

Participants

4

Reactant 1

HCID 86701392HCID 86701392, compound

Product 1

HCID 86701394HCID 86701394, compoundYield 90.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (2S,5R)-6-(benzyloxy)-2-(5-morpholino-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (0.12 g) and 10% Pd/C (70 mg) in THF (5 mL) was stirred at rt under H2 atmosphere for 1-2 hrs. The reaction mixture was then filtered and concentrated to afford (2S,5R)-6-hydroxy-2-(5-morpholino-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one (83 mg, 90%), which was used directly in the next step. ESI-MS (EI+, m/z): 296 [M+H]+.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-52799ed376184da19e8adfce09a5900f
Source dataset
uspto-grants-2015_03
Patent number
US08969570B2

Reaction notes

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