1192651-49-2

Basic information

• Product Name: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• Synonyms: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;(1R,2S,5R)-7-Oxo-6-(phenylmethoxy)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide;(1R,2S,5R)-6-(Benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide
• CAS NO: 1192651-49-2
• Molecular Formula: C₁₄H₁₇N₃O₃
• Molecular Weight: 275.30308
• EINECS: -0
• Mol File: 1192651-49-2.mol
• Article Data: 19

Chemical Properties

• Boiling Point: 543.6±30.0 °C(Predicted)
• Appearance: /
• Density: 1.36±0.1 g/cm3(Predicted)
• PKA: 17.19±0.20(Predicted)
• CAS DataBase Reference: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(CAS DataBase Reference)
• NIST Chemistry Reference: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(1192651-49-2)
• EPA Substance Registry System: (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide(1192651-49-2)

Safety Data

• Hazardous Substances Data: 1192651-49-2(Hazardous Substances Data)

Usage

Uses

Different sources of media describe the Uses of 1192651-49-2 differently. You can refer to the following data:
1. (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.
2. (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.

Upstream product

• 81470-51-1 tert-butyl N-benzyloxycarbonyl-L-pyroglutamate 
• 1383814-59-2 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid allyl ester 
• 147489-30-3 (2S)-5-oxopiperidine-1,2-dicarboxylic acid 1-benzyl ester 2-tert-butyl ester 
• 1383814-54-7 (2S,5R)-tert-butyl 5-(benzyloxyamino)-1-(2,2,2-trifluoroacetyl)piperidine-2-carboxylate 
• 1383814-56-9 (2S,5R)-tert-butyl 6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylate 
• 1383814-58-1 (2S,5R)-6-benzyloxy-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid methyl ester 
• 1416134-73-0 (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate methyl ester 
• 1171080-44-6 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid benzyl ester 
• 1426572-83-9 trans-5-(benzyloxyamino)-2-carbamoylpiperidine-1-carboxylic acid tert-butyl ester 
• 530-62-1 1,1'-carbonyldiimidazole 
• 28920-43-6 (fluorenylmethoxy)carbonyl chloride 
• 1416134-49-0 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 

Downstream Products

• 1383814-64-9 (2S,5R)-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 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 
• 1192500-31-4 (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate 
• 1471297-88-7 (2S,5R)-6-(benzyloxy)-2-(1,2,4-oxadiazol-5-yl)-1,6-diazabicyclo[3.2.1]octan-7-one 
• 1471297-86-5 (2S,5R,Z)-6-(benzyloxy)-N-((dimethylamino)methylene)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 

Relevant articles and documents

Preparation method of avibactam sodium

The invention discloses a synthesis method of avibactam sodium. (2S,5R)-benzyloxyamino piperidine-2-ethyl formate oxalate (I) is used as an initial raw material; and the method comprises the followingsteps: reacting the raw material with a protecting group, carrying out carbonylation cyclization, carrying out hydrolysis of ester, ammoniating, sulfonating with a sulfur trioxide complex, salifyingwith an ammonium ion source, and salifying with a sodium salt to obtain avibactam sodium, and has the advantages of simple operation, easily controlled conditions, easy industrial production and wideapplication prospect.

Simple and convenient preparation method of avibatan intermediate

The invention discloses a simple and convenient preparation method of an avibatan intermediate. The simple and convenient preparation method of the avibatan intermediate includes the steps that a typeIII compound is taken as a raw material, hydrolyzed under the alkaline condition, and then acidized to prepared a type IV compound, the obtained type IV compound and striphosgene or diphosgene are subjected to cyclic urea and acylating chlorination reactions simultaneously in the presence of an organic base and a catalyst, a type V compound is obtained, and a final product (II) is then obtained after amidation. According to the simple and convenient preparation method of the avibatan intermediate, the cyclic urea, acylating chlorination and amidation reactions are completed by a 'one pot method', and intermediate products do not need to be separated and purified; and raw materials are cheap and easy to get, the process is simple, operability is high, no special protective agent and carbonylation reagent are required, the reaction atom economical efficiency is high, the cost is low, the production process is environment friendly, the purity of the obtained product (II) is high, the yield is high, and cost reduction and environment-friendly production of an avibatan (I) is facilitated.

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.