1174020-21-3

Basic information

• Product Name: 4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl]carbonyl}amino)piperidine-1-carboxylic acid benzyl ester
• Synonyms: 4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl]carbonyl}amino)piperidine-1-carboxylic acid benzyl ester
• CAS NO: 1174020-21-3
• Molecular Weight: 492.575
• Mol File: 1174020-21-3.mol

Chemical Properties

• CAS DataBase Reference: 4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl]carbonyl}amino)piperidine-1-carboxylic acid benzyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl]carbonyl}amino)piperidine-1-carboxylic acid benzyl ester(1174020-21-3)
• EPA Substance Registry System: 4-({[(2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-yl]carbonyl}amino)piperidine-1-carboxylic acid benzyl ester(1174020-21-3)

Safety Data

• Hazardous Substances Data: 1174020-21-3(Hazardous Substances Data)

Upstream product

• 1174020-20-2 benzyl 4-[({(2S,5R)-5-[(benzyloxy)amino]piperidin-2-yl}carbonyl)amino]piperidine-1-carboxylate mono-tosylate 
• 120278-07-1 benzyl 4-aminopiperidine-1-carboxylate 
• 1174020-67-7 tert-butyl (2S)-2-[({1-[(benzyloxy)carbonyl]piperidin-4-yl}amino)carbonyl]-5-oxopiperidine-1-carboxylate 
• 1174020-15-5 benzyl 4-{[1-(tert-butoxycarbonyl)-5-oxo-L-prolyl]amino}piperidinecarboxylate 
• 1401540-68-8 4-[({(2S,5S)-5-[(benzyloxy)amino]piperidin-2-yl}carbonyl)amino ]piperidine-1-carboxylic acid benzyl ester 
• 1174020-16-6 benzyl 4-({N-(tert-butoxycarbonyl)-6-[dimethyl(oxido)-λ(4)-sulfanylidene]-5-oxo-L-norleucyl}amino)piperidine-1-carboxylate 
• 1174020-17-7 tert-butyl (2S)-2-[({1-[(benzyloxy)carbonyl]piperidin-4-yl}amino)carbonyl]-5-oxopiperidine-1-carboxylate 
• 1174020-18-8 tert-butyl (2S,5S)-2-[({1-[(benzyloxy)carbonyl]piperidin-4-yl}amino)carbonyl]-5-({[4-(trifluoromethyl)phenyl]sulfonyl}oxy)piperidine-1-carboxylate 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 1174020-66-6 C₁₈H₂₃N₃O₄ 
• 79722-21-7 tert-butyl N-(benzyloxy)carbamate 
• 98-79-3 L-Pyroglutamic acid 
• 1174020-19-9 4-[({(2S,5R)-5-[(benzyloxy)amino]-piperidine-2-yl}carbonyl)amino]piperidine-1-carboxylic acid benzyl ester 

Downstream Products

• 1174018-99-5 (2S,5R)-sulfuric acid mono{[(4-aminopiperidin-4-yl)carbonyl]-7-oxo-1,6-diazabicyclo[3.2.1]oct-6-yl}ester 

Relevant articles and documents

Safe and Efficient Phosgenation Reactions in a Continuous Flow Reactor

Phosgene is widely used in organic synthesis owing to its high reactivity, utility, and cost efficiency. However, the use of phosgene in batch processes on the industrial scale is challenging owing to its toxicity. An effective method to minimize reaction volumes and mitigate the safety risks associated with hazardous chemicals is the use of flow reactors. Consequently, we have established a flow reaction system using triphosgene and tributylamine, which affords a homogeneous reaction that avoids clogging issues. In addition, we have demonstrated that this methodology can be applied to a wide variety of phosgene reactions, including the preparation of pharmaceutical intermediates, in good to excellent yields.

PROCESS FOR PRODUCING ORGANIC COMPOUND

The present disclosure provides a reaction of a chlorine-containing compound using a flow reactor which is less restricted by a solvent to be used. In the present disclosure, an organic compound is produced by supplying a reaction substrate having at least one functional group which can react with chlorine and is selected from the group consisting of hydroxy group, a thiol group, an amino group, a carboxyl group, a thiocarboxyl group, and an acid amide group, and a chlorine-containing compound to a flow reactor together with a trialkyl amine having 9 to 40 carbon atoms and an organic solvent, and allowing the reaction substrate and the chlorine-containing compound to react with each other.

METHOD FOR PRODUCING OPTICALLY ACTIVE BICYCLIC UREA COMPOUND

A problem to be solved by the present invention is to provide a process for producing an optically active bicyclic urea compound useful as an intermediate for β-lactamase inhibitor, in a simple and easy manner with high efficiency. The present invention includes reacting a specific ester compound with a specific amine in the presence of a metal alkoxide and/or an alkaline earth metal salt to produce the corresponding amide compound, which is then reacted with phosgene or a phosgene equivalent, followed by, if necessary, treatment with an acid or a base, to produce an optically active bicyclic urea compound. This makes it possible to produce an optically active bicyclic urea compound in a simple and easy manner with high efficiency and in high optical purity, without using expensive reagents such as catalysts and condensation agents, and without passing through protection and deprotection steps.

A concise synthesis of a β-lactamase inhibitor

MK-7655 (1) is a β-lactamase inhibitor in clinical trials as a combination therapy for the treatment of bacterial infection resistant to β-lactam antibiotics. Its unusual structural challenges have inspired a rapid synthesis featuring an iridium-catalyzed N-H insertion and a series of late stage transformations designed around the reactivity of the labile bicyclo[3.2.1]urea at the core of the target.

BETA-LACTAMASE INHIBITORS

Substituted bicyclic beta-lactams of Formula I: (I), are ?-lactamase inhibitors, wherein a, X, R1 and R2 are defined herein. The compounds and pharmaceutically acceptable salts thereof are useful in the treatment of bacterial infections in combination with ?-lactam antibiotics. In particular, the compounds can be employed with a ?-lactam antibiotics (e.g., imipenem, piperacillin, or ceftazidime) against microorganisms resistant to ?-lactam antibiotics due to the presence of the ?-lactamases.