Avibactam Impurity 15

Base Information

• Chemical Name: Avibactam Impurity 15
• CAS No.: 1416134-60-5
• Molecular Formula: C15H20N2O3
• Molecular Weight: 276.335
• Mol file: 1416134-60-5.mol

Synonyms:Avibactam Impurity 15

Chemical Property of Avibactam Impurity 15

Chemical Property:

• Boiling Point: 401.6±55.0 °C(Predicted)
• PKA: 6.66±0.40(Predicted)
• PSA: 59.92000
• Density: 1.17±0.1 g/cm3(Predicted)
• LogP: 2.20310

Purity/Quality:

99%+, ^*data from raw suppliers

(2S)-5-[(Phenylmethoxy)imino]-2-piperidinecarboxylicAcidEthylEster ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (2S)-5-[(Phenylmethoxy)imino]-2-piperidinecarboxylic Acid Ethyl Ester 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.

Technology Process of Avibactam Impurity 15

There total 10 articles about Avibactam Impurity 15 which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 98.5%

O-benzylhydroxylamine hydrochloride + piperidine-5-one-2S-carboxylic acid ethyl ester → 5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester (1416134-60-5)

Guidance literature:

With triethylamine; In 1,2-dichloro-ethane; at 50 - 55 ℃; for 4h;

Reference yield: 98.5%

piperidine-5-one-2S-carboxylic acid ethyl ester + O-benzylhydoxylamine hydrochloride (2687-43-6) → 5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester (1416134-60-5)

Guidance literature:

With triethylamine; In 1,2-dichloro-ethane; at 50 - 55 ℃; for 4h;

Reference yield: 98.3%

ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt (1416134-48-9) → 5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester (1416134-60-5)

Guidance literature:

ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt; With sodium hydroxide; In methanol; water; ethyl acetate; 1,2-dichloro-benzene; at 0 - 5 ℃; for 3h;

With di-tert-butyl peroxide; at 20 - 25 ℃; for 3h;

upstream raw materials:

(S)-ethyl N-tert-butoxycarbonylpyroglutamate

ethyl (S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ⁶-sulfanylidene)-5-oxohexanoate

C₂₀H₂₉ClN₂O₅

ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt

Downstream raw materials:

ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt

(2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate

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

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

Refernces

• 1、 -. "A method of recovering and utilizing avibactam intermediate production waste liquid". Paragraph 0060; 0061. . Retrieved 2018/03/01.
• 2、 -. "PROCESSES FOR PREPARING HETEROCYCLIC COMPOUNDS INCLUDING TRANS-7-OXO-6-(SULPHOOXY)-1,6-DIAZABICYCLO[3,2,1]OCTANE-2-CARBOXAMIDE AND SALTS THEREOF". . . Retrieved 2013/02/27.