Acetic Acid → HCID 86701382, compound
Reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[OH:25][C:26]([C:28](F)(F)F)=O.[CH2:32]([O:39][N:40]1[C:46](=[O:47])[N:45]2[CH2:48][C@H:41]1[CH2:42][CH2:43][C@H:44]2[C:49]([NH:51][NH2:52])=[O:50])[C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.C(O)(=O)C.CCN(C(C)C)C(C)C>CN(C=O)C>[C:26]([N:51]([C:49]([C@@H:44]1[CH2:43][CH2:42][C@@H:41]2[CH2:48][N:45]1[C:46](=[O:47])[N:40]2[O:39][CH2:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:50])[NH2:52])(=[O:25])[CH3:28]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 0 °C
Procedure
HATU (0.90 g, 2.48 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide TFA salt (1.0 g, 2.48 mmol), acetic acid (0.12 g, 2.07 mmol) and DIPEA (1.1 μg, 8.3 mmol) in dry DMF (10 mL) at 0° C. The reaction mixture was stirred at 0° C. for 1 h. The mixture was then quenched with saturated sodium chloride (50 mL) and exacted with EtOAc (3×). The combined organic layer was washed with saturated sodium chloride (2×), dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (gradient elution 10:1 to 1:10 petroleum ether/EtOAc) to afford (2S,5R)—N-acetyl-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide (0.6 g, 73%). ESI-MS (EI+, m/z): 333 [M+H]+.
Workup
- customThe mixture was then quenched with saturated sodium chloride (50 mL)
- washThe combined organic layer was washed with saturated sodium chloride (2×)
- dry with materialdried over Na2SO4
- concentrationconcentrated
- customThe residue was purified by silica gel column chromatography (gradient elution 10:1 to 1:10 petroleum ether/EtOAc)
Sources & evidence
- ORD record
- ord-3ff389cc11904e06826524216ccb9712
- Source dataset
- uspto-grants-2015_03
- Patent number
- US08969570B2
Reaction notes
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