Trifluoroacetic acid → (5R)-2-(5-(1-(aminomethyl)cyclopropyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one

HRID 1430698Notes

Reaction equation

HRID 1430698 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][CH2:15][C:16]1([C:19]2[O:20][C:21]([CH:24]3[CH2:30][CH2:29][C@@H:28]4[CH2:31][N:25]3[C:26](=[O:40])[N:27]4[O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:22][N:23]=2)[CH2:18][CH2:17]1)(C)(C)C>C(Cl)Cl>[NH2:14][CH2:15][C:16]1([C:19]2[O:20][C:21]([CH:24]3[CH2:30][CH2:29][C@@H:28]4[CH2:31][N:25]3[C:26](=[O:40])[N:27]4[O:32][CH2:33][C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)=[N:22][N:23]=2)[CH2:17][CH2:18]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86701028tert-butyl(1-(5-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)cyclopropyl)methylcarbamate

Product 1

HCID 86701031(5R)-2-(5-(1-(aminomethyl)cyclopropyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-oneYield 111.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

TFA (30 mL) was added to a 0° C. solution of tert-butyl(1-(5-((5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)-1,3,4-oxadiazol-2-yl)cyclopropyl)methylcarbamate (8 g, 0.017 mol) in DCM (100 mL). The mixture was allowed to warm to rt and was stirred at rt for 1 h. The mixture was concentrated and the residue was washed with Et2O (50 mL), and then filtrated to afford (5R)-2-(5-(1-(aminomethyl)cyclopropyl)-1,3,4-oxadiazol-2-yl)-6-(benzyloxy)-1,6-diaza-bicyclo[3.2.1]octan-7-one (7 g, 99%), which was used directly in the next step. ESI-MS (EI+, m/z): 370.2 [M+H]+.

Workup

  1. concentrationThe mixture was concentrated
  2. washthe residue was washed with Et2O (50 mL)
  3. filtrationfiltrated

Sources & evidence

ORD record
ord-de6417b6890d4e66a86ac748fe2117ab
Source dataset
uspto-grants-2015_01
Patent number
US08940897B2

Reaction notes

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