1416134-60-5

Basic information

• Product Name: Avibactam Impurity 15
• Synonyms: Avibactam Impurity 15
• CAS NO: 1416134-60-5
• Molecular Formula: C₁₅H₂₀N₂O₃
• Molecular Weight: 276.3309
• Mol File: 1416134-60-5.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 401.6±55.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: 6.66±0.40(Predicted)
• CAS DataBase Reference: Avibactam Impurity 15(CAS DataBase Reference)
• NIST Chemistry Reference: Avibactam Impurity 15(1416134-60-5)
• EPA Substance Registry System: Avibactam Impurity 15(1416134-60-5)

Safety Data

• Hazardous Substances Data: 1416134-60-5(Hazardous Substances Data)

Usage

Description

Afibactam Impurity 15, also known as (2S)-5-[(Phenylmethoxy)imino]-2-piperidinecarboxylic Acid Ethyl Ester, is an impurity found in Avibactam (A794850, Na Salt), a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam is known for its irreversible inhibition of lactamase from Mycobacterium tuberculosis, making it a significant compound in the field of antibiotic resistance.

Uses

Used in Pharmaceutical Industry:
Afibactam Impurity 15 is used as an impurity in the development and production of Avibactam, a novel β-lactamase inhibitor. Its presence is crucial for understanding the overall effectiveness, safety, and quality control of Avibactam as a pharmaceutical compound. By studying and managing the presence of this impurity, researchers and manufacturers can ensure the optimal performance of Avibactam in combating antibiotic-resistant bacteria, particularly those associated with Mycobacterium tuberculosis infections.

Upstream product

• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 56-86-0 L-glutamic acid 
• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 1416134-59-2 C₂₀H₂₉ClN₂O₅ 
• 1416134-58-1 ethyl (S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ⁶-sulfanylidene)-5-oxohexanoate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 

Downstream Products

• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 1192500-31-4 (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate 
• 1192651-49-2 (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192491-61-4 (2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt 
• 1416134-49-0 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide 
• 1192651-80-1 ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt 
• 1416134-63-8 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester 
• 1416134-47-8 (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate 

Relevant articles and documents

Method of preparing 5R-[(benzyloxy) amino] piperidine-2S-carboxylic acid or a derivative thereof

The present application relates to methods of preparing 5R-[(benzyloxy) amino] piperidine-2S-carboxylic acid or its derivatives in an environment-friendly way. The method uses L-glutamic acid as a starting material, which is first subjected to esterification reaction in the presence of an acidic reagent, and then reacted successively with 2-haloacetate and N-protecting agent, or with N-protecting agent and 2-haloacetate under a basic condition to obtain compound IV; then, the obtained compound IV is subjected to intramolecular condensation into a ring under the action of a strong base to obtain N-protecting group piperidine-5-one-2S-carboxylate (V).

A method of recovering and utilizing avibactam intermediate production waste liquid

The invention relates to a method of recovering and utilizing avibactam intermediate production waste liquid. The waste liquid produced in a production process of an avibactam intermediate that is 5R-benzyloxyaminopiperidine-2S-formateoxalate IIb is adopted as an initial raw material, and is oxidized to generate 5R-benzyloxyiminopiperidine-2S-formate III; the compound III is subjected to selectivereduction, chiral crystallization resolution and filtration to obtain the solid 5R-benzyloxyaminopiperidine-2S-formateoxalateoxalate IIb; and the obtained filtrate is subjected to the oxidation, reduction and resolution steps again. The compound IIb is neutralized to prepare 5R-benzyloxyaminopiperidine-2S-formate IIa, and the compound IIa or the compound IIb can be utilized to prepare avibactam I. The method is simple and convenient to operate, the atom utilization rate is increased, and the total yield of the compound IIb can be 99.0% or above, thus facilitating cost reduction, facilitatingreduction of avibactam waste liquid and facilitating environment protection.