1463501-46-3

Basic information

• Product Name: 1-tert-butyl 2-ethyl (2R,5S)-5-[(benzyloxy)amino]piperidine-1,2-dicarboxylate
• CAS NO: 1463501-46-3
• Molecular Weight: 378.469
• Mol File: 1463501-46-3.mol
• Article Data: 12

Chemical Properties

• CAS DataBase Reference: 1-tert-butyl 2-ethyl (2R,5S)-5-[(benzyloxy)amino]piperidine-1,2-dicarboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: 1-tert-butyl 2-ethyl (2R,5S)-5-[(benzyloxy)amino]piperidine-1,2-dicarboxylate(1463501-46-3)
• EPA Substance Registry System: 1-tert-butyl 2-ethyl (2R,5S)-5-[(benzyloxy)amino]piperidine-1,2-dicarboxylate(1463501-46-3)

Safety Data

• Hazardous Substances Data: 1463501-46-3(Hazardous Substances Data)

Usage

Explanation

This is the full chemical name of the compound, also known as TEBP.

Explanation

The abbreviation for the compound, used for ease of reference.

Explanation

TEBP belongs to the class of compounds derived from piperidine, which is a heterocyclic organic compound.

Explanation

TEBP is commonly employed as an intermediate in the synthesis of various pharmaceutical drugs.

Explanation

TEBP has shown potential as an effective agent in treating mental disorders such as psychosis and depression.

Explanation

TEBP's structure allows it to easily cross the blood-brain barrier, making it a promising candidate for central nervous system drug development.

Explanation

TEBP has demonstrated the ability to reduce inflammation and relieve pain, making it a versatile compound with potential therapeutic applications.

Explanation

TEBP's unique chemical structure and pharmacological properties make it an important and valuable compound in the field of pharmaceutical research and development.

Chemical class

Piperidine derivative

Use

Pharmaceutical industry intermediate

Potential therapeutic applications

Antipsychotic and antidepressant agent

Ability to cross the blood-brain barrier

Yes

Additional properties

Anti-inflammatory and analgesic

Importance

Valuable in pharmaceutical research and development

Upstream product

• 24424-99-5 di-tert-butyl dicarbonate 
• 144978-12-1 1-tert-butyl 2-ethyl (2R)-5-oxopyrrolidine-1,2-dicarboxylate 
• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 65275-12-9 5-hydroxy-2-picolinic acid ethyl ester 
• 622-33-3 N-benzyloxyamine 
• 1416134-47-8 (2S,5R)?5?[(benzyloxy)amino]piperidine?2?carboxylate 
• 695183-75-6 (2S,5S)-5-hydroxypiperidin-2-carboxylic acid methyl ester 
• 63088-78-8 (2S,5R)-5-hydroxypiperidine-2-carboxylic acid 
• 1426573-07-0 (2S,5R)-1-[(1,1-dimethylethyl)carbonyl]-5-[(benzyloxy)amino]piperidine-2-carboxylic acid 
• 75-03-6 ethyl iodide 
• 1463501-45-2 (2S,5R)-1-tert-butyl 2-ethyl 5-(N-(benzyloxy)-(2-nitrophenyl)sulfonamido)piperidine-1,2-dicarboxylate 
• 77925-80-5 N-(2-Nitrophenylsulfonyl)-O-(phenylmethyl)hydroxylamine 
• 2687-43-6 O-benzylhydoxylamine hydrochloride 
• 208519-98-6 (S)-ethyl 2-(((tert-butoxy)carbonyl)amino)-6-diazo-5-oxohexanoate 

Downstream Products

• 1426572-83-9 trans-5-(benzyloxyamino)-2-carbamoylpiperidine-1-carboxylic acid tert-butyl ester 
• 1174020-25-7 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 
• 2064219-13-0 (2R,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxylic acid 

Relevant articles and documents

MODULATORS OF THE INTEGRATED STRESS RESPONSE PATHWAY

The present invention relates to compounds of formula (I) or pharmaceutically acceptable salts, solvates, hydrates, tautomers or stereoisomers thereof, wherein R1, R2, R2a, R3, Ra2, Ra4, R

Use of Lipase Catalytic Resolution in the Preparation of Ethyl (2 S,5 R)-5-((Benzyloxy)amino)piperidine-2-carboxylate, a Key Intermediate of the β-Lactamase Inhibitor Avibactam

Here we describe an efficient and cost-effective chemoenzymatic synthesis of the β-lactamase inhibitor avibactam starting from commercially available ethyl 5-hydroxypicolinate hydrochloride. Avibactam was synthesized in 10 steps with an overall yield of 23.9%. The synthetic route features a novel lipase-catalyzed resolution step during the preparation of (2S,5S)-ethyl 5-hydroxypiperidine-2-carboxylate, a valuable precursor of the key intermediate ethyl (2S,5R)-5-((benzyloxy)amino)piperidine-2-carboxylate. Our synthetic route was used to produce 400 g of avibactam sodium salt.

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.