HCID 178454255, compound → HCID 178454256, compound

HRID 1855160Notes

Reaction equation

HRID 1855160 reaction equation
[C:1]([O:5][C:6]([N:8]=[C:9]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])[NH:10][CH2:11][CH2:12][C:13]1[O:17][C:16]([C@@H:18]2[CH2:24][CH2:23][C@@H:22]3[CH2:25][N:19]2[C:20](=[O:34])[N:21]3[O:26]CC2C=CC=CC=2)=[N:15][N:14]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>C1COCC1.[Pd]>[OH:26][N:21]1[C:20](=[O:34])[N:19]2[CH2:25][C@H:22]1[CH2:23][CH2:24][C@H:18]2[C:16]1[O:17][C:13]([CH2:12][CH2:11][NH:10][C:9]([NH:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37])=[N:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])=[N:14][N:15]=1

Participants

4

Reactant 1

HCID 178454255HCID 178454255, compound

Product 1

HCID 178454256HCID 178454256, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (2S,5R)-2-(5-((2,3-bis(tert-butoxycarbonyl)guanidino)ethyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (80 mg, 0.136 mmol) in THF (15 mL) was added 10% Pd/C (45 mg) and the mixture was stirred under H2 atmosphere at rt for 1 h. The reaction mixture was filtered and concentrated to afford (2S,5R)-6-hydroxy-2-(5-((2,3-bis(tert-butoxycarbonyl)guanidino)ethyl)-1,3,4-oxadiazol-2-yl)-1,6-diaza-bicyclo[3.2.1]octan-7-one, which was directly used in the next step. ESI-MS (EI+, m/z): 496.2 [M+H]+.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-5ee038470abe44c78a3ba0daa183a5ff
Source dataset
uspto-grants-2015_02
Patent number
US08962843B2

Reaction notes

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