1133931-74-4

Basic information

• Product Name: 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)imino]-, phenylmethyl ester, (2S)-
• Synonyms: 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)imino]-, phenylmethyl ester, (2S)-;benzyl(S)-5-((benzyloxy)imino)piperidine-2-carboxylate;(2S)-5-(benzyloxyimino)-piperidine-2-carboxylic acid benzyl ester
• CAS NO: 1133931-74-4
• Molecular Formula: C₂₀H₂₂N₂O₃
• Molecular Weight: 338.40028
• Mol File: 1133931-74-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 487.8±55.0 °C(Predicted)
• Appearance: /
• Density: 1.17±0.1 g/cm3(Predicted)
• PKA: 6.50±0.40(Predicted)
• CAS DataBase Reference: 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)imino]-, phenylmethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)imino]-, phenylmethyl ester, (2S)-(1133931-74-4)
• EPA Substance Registry System: 2-Piperidinecarboxylic acid, 5-[(phenylmethoxy)imino]-, phenylmethyl ester, (2S)-(1133931-74-4)

Safety Data

• Hazardous Substances Data: 1133931-74-4(Hazardous Substances Data)

Upstream product

• 1171080-45-7 (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 
• 622-33-3 N-benzyloxyamine 
• 1401540-62-2 (2S,5S)-5-(benzyloxyamino)-piperidine-2-carboxylic acid benzyl ester 
• 1133931-73-3 benzyl (2S)-5-[(benzyloxy)imino]-2-{[(tert-butoxy)carbonyl]amino}-6-chlorohexanoate 
• 113400-36-5 benzyl (2S)-N-tert-butoxycarbonyl-5-oxoprolinate 

Downstream Products

• 1171080-45-7 (2S,5R)-5-benzyloxyaminopiperidin-2-carboxylic acid benzyl ester oxalic acid salt 
• 1192500-31-4 (2S,5R)-2-carbamoyl-7-oxo-1,6-diazabicylco[3.2.1]octan-6-yl hydrogensulfate 
• 1192651-49-2 (1R,2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 
• 1192491-61-4 (2S,5R)-1,6-diazabicyclo[3.2.1]octane-2-carboxamide 7-oxo-6-(sulfoxy)monosodium salt 
• 1192650-82-0 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid benzyl ester 
• 1416134-49-0 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid amide 
• 1192651-80-1 ({[(2S,5R)-2-carbamoyl-7-oxo-6-(sulfooxy)-1,6-diazabicyclo[3,2,1]-oct-6-yl]oxy}sulfonyl)tetrabutylammonium salt 
• 1416134-48-9 ethyl (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxylate oxalic acid salt 
• 1416134-50-3 (2S,5R)-5-[(benzyloxy)amino]piperidine-2-carboxamide ethanedioate 
• 1416134-63-8 (2S,5R)-6-(benzyloxy)-7-oxo-1,6-diazabicyclo[3.2.1]octan-2-carboxylic acid ethyl ester 
• 1171080-44-6 (2S,5R)-5-(benzyloxyamino)-piperidine-2-carboxylic acid benzyl ester 
• 1401540-62-2 (2S,5S)-5-(benzyloxyamino)-piperidine-2-carboxylic acid benzyl ester 

Relevant articles and documents

Recycling method of avibactam intermediate isomer

The invention relates to a recycling method of an avibactam intermediate isomer, belonging to the technical fields of pharmaceutical synthesis and recycling. According to the pharmaceutical synthesis,the existing complex recycling problem is solved. The recycling method comprises the following steps: reacting by virtue of (2S,5S)-5-((benzyloxy)amino)piperidine-2-carboxylate and an amino protection group Boc2O in the presence of weakly alkaline substances, so as to generate an intermediate product; carrying out catalytic hydrogenation reduction reaction in the presence of a palladium-containing catalyst; carrying out oxidation reaction under the effect of an oxidant, so as to obtain a corresponding ketone intermediate product; and carrying out condensation reaction on a compound represented by a formula I (shown in the description) and benzyloxyamine hydrochloride in the presence of an acid-binding agent, and carrying out deprotection reaction, so as to obtain a final product, namely the compound of the formula I. The recycling method has the advantages that the recycling is efficient, the process route is simple, reaction conditions are mild, and the environmental pollution is low.

A method of recovering and utilizing avibactam intermediate production waste liquid

The invention relates to a method of recovering and utilizing avibactam intermediate production waste liquid. The waste liquid produced in a production process of an avibactam intermediate that is 5R-benzyloxyaminopiperidine-2S-formateoxalate IIb is adopted as an initial raw material, and is oxidized to generate 5R-benzyloxyiminopiperidine-2S-formate III; the compound III is subjected to selectivereduction, chiral crystallization resolution and filtration to obtain the solid 5R-benzyloxyaminopiperidine-2S-formateoxalateoxalate IIb; and the obtained filtrate is subjected to the oxidation, reduction and resolution steps again. The compound IIb is neutralized to prepare 5R-benzyloxyaminopiperidine-2S-formate IIa, and the compound IIa or the compound IIb can be utilized to prepare avibactam I. The method is simple and convenient to operate, the atom utilization rate is increased, and the total yield of the compound IIb can be 99.0% or above, thus facilitating cost reduction, facilitatingreduction of avibactam waste liquid and facilitating environment protection.

Development of a Manufacturing Route to Avibactam, a β-Lactamase Inhibitor

Process development work to provide an efficient, robust, and cost-effective manufacturing route to avibactam, a β-lactamase inhibitor is presented herewith. Aspects of this optimization work include the counterintuitive introduction of a protecting group to effect a difficult urea formation and the use of controlled feed hydrogenation conditions to facilitate an elegant one pot debenzylation and sulfation reaction. Overall, the commercial process delivers avibactam in much improved yield with significant reduction in the environmental footprint.