Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate

Base Information

• Chemical Name: Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate
• CAS No.: 1171080-45-7
• Molecular Formula: C20H24N2O3.C2H2O4
• Molecular Weight: 430.458
• Mol file: 1171080-45-7.mol

Synonyms:Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate;2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)amino]-, phenylmethyl ester, (2S,5R)- (ethanedioate);(2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylic acid benzyl ester ethanedioate;(2S,5R)-5-Benzyloxyamino-piperidine-2-carboxylic acid benzyl ester oxalate;(2S,5R)-5-[(Phenylmethoxy)amino]-2-piperidinecarboxylic acid phenylmethyl ester ethanedioate;(2S,5R)-Benzyl 5-((benzyloxy)amino)piperidine-2-carboxylate oxalate;benzyl(2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylateoxalate

Chemical Property of Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate

Chemical Property:

• PSA: 134.19000
• LogP: 2.44710
• Storage Temp.: Inert atmosphere,Room Temperature

Purity/Quality:

99.9% ^*data from raw suppliers

(2S,5R)-Benzyl5-((Benzyloxy)amino)piperidine-2-carboxylateOxalate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (2S,5R)-Benzyl 5-((benzyloxy)amino)piperidine-2-carboxylate Oxalate is used as a reactant in the synthesis of Avibactam.

Technology Process of Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate

There total 14 articles about Benzyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate ethanedioate 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: 69.0%

(2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester (1133931-74-4) + oxalic acid (144-62-7,97993-78-7) → (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt (1171080-45-7,1416134-44-5)

Guidance literature:

(2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl 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: 37.7%

(2S)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester (1133931-68-6) + oxalic acid (144-62-7,97993-78-7) → (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt (1171080-45-7,1416134-44-5)

Guidance literature:

In methanol; at 0 - 45 ℃; for 6h;

Reference yield:

2-benzyl 1-tert-butyl (2S)-5-[(benzyloxy)imino]piperidine-1,2-dicarboxylate + oxalic acid (144-62-7,97993-78-7) → (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt (1171080-45-7,1416134-44-5)

Guidance literature:

2-benzyl 1-tert-butyl (2S)-5-[(benzyloxy)imino]piperidine-1,2-dicarboxylate; With sodium tris(acetoxy)borohydride; trifluoroacetic acid; In ethyl acetate; at -5 - 0 ℃; for 6h; Green chemistry; Large scale;

oxalic acid; for 5h; Green chemistry; Large scale;

upstream raw materials:

(2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester

oxalic acid

benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate

(2S)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester 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)-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.
• 2、 Ball, Matthew,Boyd, Alistair,Ensor, Gareth J.,Evans, Matthew,Golden, Michael,Linke, Simon R.,Milne, David,Murphy, Rebecca,Telford, Alex,Kalyan, Yuriy,Lawton, Graham R.,Racha, Saibaba,Ronsheim, Melanie,Zhou, Shao Hong. "Development of a Manufacturing Route to Avibactam, a β-Lactamase Inhibitor". . p. 1799 - 1805. Retrieved 2016/10/31.