1416134-49-0

Basic information

• Product Name: (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide
• Synonyms: (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide;2-Piperidinecarboxamide, 5-[(phenylmethoxy)amino]-, (2S,5R)-;(2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide;(2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxamide;Avibactam Intermediate 2
• CAS NO: 1416134-49-0
• Molecular Formula: C₁₃H₁₉N₃O₂
• Molecular Weight: 249.30886
• EINECS: -0
• Mol File: 1416134-49-0.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 463.1±55.0 °C(Predicted)
• Appearance: /
• Density: 1.18±0.1 g/cm3(Predicted)
• Storage Temp.: Keep in dark place,Sealed in dry,Room Temperature
• PKA: 16.69±0.40(Predicted)
• CAS DataBase Reference: (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide(1416134-49-0)
• EPA Substance Registry System: (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide(1416134-49-0)

Safety Data

• Hazardous Substances Data: 1416134-49-0(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1416134-49-0 differently. You can refer to the following data:
1. (2S,5R)-5-[(benzyloxy)amino]piperidine-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.
2. (2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxamide 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.

Upstream product

• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 
• 144978-35-8 (S)-ethyl N-tert-butoxycarbonylpyroglutamate 
• 1133931-74-4 (2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester 
• 1416134-44-5 (2S)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 
• 1133931-73-3 benzyl (2S)-5-[(benzyloxy)imino]-2-{[(tert-butoxy)carbonyl]amino}-6-chlorohexanoate 
• 1171080-45-7 (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 
• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 1416134-74-1 methyl (2S,5R)-5-benzyloxyaminopiperidine-2-carboxylate oxalate 
• 1416134-58-1 ethyl (S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ⁶-sulfanylidene)-5-oxohexanoate 
• 1416134-59-2 C₂₀H₂₉ClN₂O₅ 
• 1416134-60-5 5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester 
• 65275-12-9 5-hydroxy-2-picolinic acid ethyl ester 
• 1463501-46-3 (2S,5R)-5-(benzyloxyamino)piperidin-1,2-dicarboxylic acid 1-tert-butyl ester 2-ethyl ester 
• 1416134-47-8 (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate 

Downstream Products

• 1192651-49-2 (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192500-31-4 (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate 
• 1192500-31-4 (2S,5R)-6-(sulfoxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1383814-64-9 (1R,2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192491-61-4 sulfuric acid [(1R,2S,5R)-2-aminocarbonyl-7-oxo-1,6-azabicyclo[3.2.1]oct-6-yl]ester sodium salt 
• 1192651-80-1 ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt 
• 1192491-61-4 (2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt 

Relevant articles and documents

Preparation method of avibactam intermediate

The invention relates to a preparation method of an avibactam intermediate. The preparation method comprises the following steps: mixing a compound with a structure as shown in a formula 2, a chiral catalyst, an acid and a solvent, and stirring to prepare a compound with a structure as shown in a formula 1; the chiral catalyst has a structure as shown in a formula (I). The method is high in yield,purity and chiral purity, and is environment-friendly.

RETRACTED ARTICLE: A New Synthetic Route to Avibactam: Lipase Catalytic Resolution and the Simultaneous Debenzylation/Sulfation

An efficient synthesis of avibactam starting from commercially available ethyl-5-hydroxypicolinate was completed in 10 steps and 23.9% overall yield. The synthesis features a novel lipase-catalyzed resolution, in the preparation of (2S,5S)-5-hydroxypiperidine-2-carboxylate acid, which is a valuable precusor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. An optimized one-pot debenzylation/sulfation reaction, followed by cation exchange, gave the avibactam sodium salt on a 400.0 g scale.

Development of a Manufacturing Route to Avibactam, a β-Lactamase Inhibitor

Process development work to provide an efficient, robust, and cost-effective manufacturing route to avibactam, a β-lactamase inhibitor is presented herewith. Aspects of this optimization work include the counterintuitive introduction of a protecting group to effect a difficult urea formation and the use of controlled feed hydrogenation conditions to facilitate an elegant one pot debenzylation and sulfation reaction. Overall, the commercial process delivers avibactam in much improved yield with significant reduction in the environmental footprint.