Avibactam INT 1

Base Information

• Chemical Name: Avibactam INT 1
• CAS No.: 1416134-48-9
• Molecular Formula: C15H22N2O3.C2H2O4
• Molecular Weight: 368.387
• Mol file: 1416134-48-9.mol

Synonyms:Avibactam INT 1;Avibactam Intermediate;(2S,5R)-Methyl-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate (1:1);Avibactam Impurity 9;(2S,5R)-5-Methyl-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate;(2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylic acid ethyl ester ethanedioate;2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)amino]-, ethyl ester, (2S,5R)-, ethanedioate (1:1)

Chemical Property of Avibactam INT 1

Chemical Property:

• PSA: 134.19000
• LogP: 1.26680
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99% ^*data from raw suppliers

(2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylicAcidEthylEsterEthanedioate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylic Acid Ethyl Ester Ethanedioate is an impurity of Avibactam; a novel β-lactamase inhibitor with a non-lactam structural scaffold. Avibactam irreversibly inhibits lactamase from Mycobacterium tuberculosis. (2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylic Acid Ethyl Ester Ethanedioate 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 INT 1

There total 10 articles about Avibactam INT 1 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: 94.0%

ethanol (64-17-5) + (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt (1171080-45-7,1416134-44-5) + sodium ethanolate (141-52-6) + oxalic acid (144-62-7,97993-78-7) → ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt (1416134-48-9)

Guidance literature:

ethanol; (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt; sodium ethanolate; at 0 ℃; for 1h;

oxalic acid; In ethyl acetate; acetone; at 35 ℃;

Reference yield: 65.4%

5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester (1416134-60-5) + oxalic acid (144-62-7,97993-78-7) → ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt (1416134-48-9)

Guidance literature:

5-benzyloxyiminopiperidine-2S-carboxylic acid ethyl ester; With sulfuric acid; In ethyl acetate; at -20 - -15 ℃; for 1h;

With sodium tris(acetoxy)borohydride; In ethyl acetate; at -20 - -15 ℃; for 5h;

oxalic acid; In methanol; ethyl acetate; at 45 ℃; for 2h;

Reference yield:

benzyl (2S)-2-((tert-butoxycarbonyl)amino)-6-(dimethyl(oxo)-λ6-sulfanylidene)-5-oxohexanoate → ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt (1416134-48-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ethyl acetate / Reflux

2.1: methanesulfonic acid / ethyl acetate / 42 °C

2.2: 52 °C

3.1: sodium tetrahydroborate; sulfuric acid; propionic acid / ethyl acetate / -20 °C

3.3: 40 - 45 °C

4.1: 1 h / 0 °C

4.2: 35 °C

With sodium tetrahydroborate; methanesulfonic acid; sulfuric acid; propionic acid; In ethyl acetate;

upstream raw materials:

ethanol

(2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt

sodium ethanolate

oxalic acid

Downstream raw materials:

(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester

(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)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide

Refernces

• 1、 -. "A method of recovering and utilizing avibactam intermediate production waste liquid". Paragraph 0052-0054. . Retrieved 2018/03/01.