(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Chemical Properties

Boiling point:

543.6±30.0 °C(Predicted)

Density 

1.36±0.1 g/cm3(Predicted)

pka

17.19±0.20(Predicted)

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide Usage And Synthesis

Uses

(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is an impurity of Avibactam; a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam irreversibly inhibits lactamase from Mycobacterium tuberculosis.

Uses

(2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is an impurity of Avibactam (A794850, Na Salt); a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam irreversibly inhibits lactamase from Mycobacterium tuberculosis.

Synthesis

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide is synthesised using (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid as a raw material by chemical reaction. The specific synthesis steps are as follows:
DIPEA (5.8 mL, 36.2 mmol) was added to a solution of (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxylic acid (5.0 g, 18.1 mmol), EDCI (5.2 g, 27.2 mmol), HOBT (3.7 g, 27.2 mmol) and NH4Cl (1.94 g, 36.2 mmol) in DMF (60 mL) at rt. The reaction mixture was stiffed for 17 hrs, then diluted with ice water (100 mL) and extracted with EtOAc (3*). The combined organic layer was dried over Na2SO4, and concentrated. The residue was purified by silica gel column chromatography (2:1 EtOAc/petroleum ether) to afford (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diaza-bicyclo[3.2.1]octane-2-carboxamide (4.0 g, 80%) as a white solid. ESI-MS (EI+, m/z): 276 [M+H]+.

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(1192651-49-2)Related Product Information

• Avibactam INT 1
• Avibactam Impurity 15
• (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide
• Avibactam Impurity 28
• Avibactam Impurity 1
• Avibactam Impurity
• L-Norleucine, 6-chloro-N-[(1,1-dimethylethoxy)carbonyl]-5-[(phenylmethoxy)imino]-, phenylmethyl ester
• O-(Benzyloxymethyl)hydroxylamine
• POLYMYXIN B NONAPEPTIDE HYDROCHLORIDE
• Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
• Avibactam Impurity 10
• Avibactam Sodium Isomer
• Trans-5-(Benzyloxyamino)piperidine-2-carboxylic acid
• 5-HYDROXYPYRIDINE-2-CARBOXYLIC ACID ETHYL ESTER
• Avibactam Impurity
• ethyl (S)-5-oxopiperidine-2-carboxylate
• Avibactam Impurity 13
• Avibactam Impurity 4