ChemicalBook CAS DataBase List AvibactaM

AvibactaM synthesis

11synthesis methods

Product Name:AvibactaM
CAS Number:1192500-31-4
Molecular formula:C7H11N3O6S
Molecular Weight:265.24

Avibactam is a non-β-lactam β-lactamase inhibitor antibiotic, which is a new drug application for avibactam in combination with ceftazidime, and was approved by the FDA on February 25, 2015, for treating complicated urinary tract and complicated intra-abdominal Infections caused by antibiotic resistant-pathogens, including those caused by multi-drug resistant gram-negative bacterial pathogens. Synthetic Description Reference: Liu, Chengxue; Tang, Feng; Zhang, Liming. Method for synthesizing β-lactamase inhibitor Avibactam. CN 106699756. (Assignee Zibo Xinquan Pharmaceutical Technology Service Co., Ltd., Peop. Rep. China) Synthetic Description Reference: Wang, Tao; Ying, Xiaoning; Du, Liangdong; Chen, Xinzhi; Wu, Guofeng. Synthesis method of avibactam sodium as β-lactamase inhibitor. CN 108239089. (Assignee Zhejiang Medicine Co., Ltd. Xinchang Pharmaceutical Factory, Peop. Rep. China)

Synthetic Routes

ROUTE 1

ROUTE 2

Reference: Liu, Chengxue; Tang, Feng; Zhang, Liming. Method for synthesizing β-lactamase inhibitor Avibactam. CN 106699756. (Assignee Zibo Xinquan Pharmaceutical Technology Service Co., Ltd., Peop. Rep. China)

(2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide

1416134-49-0
146 suppliers
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1192500-31-4
93 suppliers
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Yield:-

Steps:

Multi-step reaction with 2 steps
1: N-ethyl-N,N-diisopropylamine; (fluorenylmethoxy)carbonyl chloride / chlorobenzene / 30 °C
2: hydrogen / 5% Pd-C / dichloromethane; N,N-dimethyl-formamide / 2250.23 Torr

References:

FOREST LABORATORIES HOLDINGS LTD. US2012/323010, 2012, A1

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

1192651-49-2
114 suppliers
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1192500-31-4
93 suppliers
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References

2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)imino]-, phenylmethyl ester, (2S)-

1133931-74-4
7 suppliers
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1192500-31-4
93 suppliers
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References

L-Norleucine, 6-chloro-N-[(1,1-dimethylethoxy)carbonyl]-5-[(phenylmethoxy)imino]-, phenylmethyl ester

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12 suppliers
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1192500-31-4
93 suppliers
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References

Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate

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1192500-31-4
93 suppliers
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References