3-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)isoxazole-5-carboxamide → 3-((2S,5R)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)isoxazole-5-carboxamide
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[CH:22]=[C:21]([C:23]([NH2:25])=[O:24])[O:20][N:19]=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[CH:22]=[C:21]([C:23]([NH2:25])=[O:24])[O:20][N:19]=1Participants
4
Reactant 1
Product 1
Reagents, catalysts & solvents 2
Procedure
A mixture of 3-((2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)isoxazole-5-carboxamide (0.25 g, 0.73 mmol) and 10% Pd/C (0.12 g) in THF (8 mL) was stirred at rt under H2 atmosphere for 2 hrs. The reaction mixture was then filtered and concentrated to afford 3-((2S,5R)-6-hydroxy-7-oxo-1,6-diaza-bicyclo[3.2.1]octan-2-yl)isoxazole-5-carboxamide (0.17 g, 90%) as a light yellow solid, which was used directly in the next step. ESI-MS (EI+, m/z): 253 [M+H]+.