93711-81-0

Basic information

• Product Name: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester
• CAS NO: 93711-81-0
• Molecular Formula: C29H27N2O10P
• Molecular Weight: 594.515
• Mol File: 93711-81-0.mol

Chemical Properties

• CAS DataBase Reference: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester(93711-81-0)
• EPA Substance Registry System: 1-Azabicyclo[3.2.0]hept-2-ene-2-carboxylic acid, 3-[(diphenoxyphosphinyl)oxy]-6-(1-hydroxyethyl)-4-methyl-7-oxo-, (4-nitrophenyl)methyl ester(93711-81-0)

Safety Data

• Hazardous Substances Data: 93711-81-0(Hazardous Substances Data)

Usage

Chemical structure

A complex molecule with a bicyclic ring containing a nitrogen atom, a carboxylic acid group, and a nitrophenyl group.

Methyl ester derivative

The compound is derived from a carboxylic acid by replacing the hydroxyl group with a methyl group.

Diphenoxyphosphinyl group

A functional group consisting of two phenoxy groups attached to a phosphorus atom.

Hydroxyethyl group

A functional group containing an ethyl group with a hydroxyl group attached.

Methyl ketone group

A functional group containing a carbonyl group bonded to a methyl group.

Upstream product

• 86978-81-6 Acetic acid (2R,3R)-3-[1-(tert-butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-1-trimethylsilanyl-azetidin-2-yl ester 
• 101765-69-9 (R)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 101765-69-9 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-thiopropionic acid S-phenyl ester 
• 104873-15-6 4-nitrobenzyl (4R,5R,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3,7-dioxo-1-azabicyclo[3.2.0]-heptane-2-carboxylate 
• 2524-64-3 chlorophosphoric acid diphenyl ester 
• 90822-25-6 p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate 
• 1499-21-4 Diphenylphosphinic chloride 
• 90822-23-4 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 
• 90822-22-3 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one 
• 90822-24-5 (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 77359-11-6 propanedioic acid mono[(4-nitrophenyl)methyl] ester 
• 90776-58-2 (S)-2-{(2S,3S)-3-[1-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-4-oxo-azetidin-2-yl}-propionic acid 

Downstream Products

• 97033-03-9 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[2-(4-nitro-benzyloxycarbonylamino)-ethylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101151-51-3 (4R,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-[(S)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 101135-08-4 (4S,5S,6S)-6-(1-Hydroxy-ethyl)-4-methyl-3-((S)-1-{1-[(E)-4-nitro-benzyloxycarbonylimino]-ethyl}-pyrrolidin-3-ylsulfanyl)-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 120764-68-3 p-Nitrobenzyl (1R,5S,6S)-2-<<(N,N-Bis(p-nitrobenzyloxycarbonyl)pyrazolidin-4-yl>thio>-6-<(1R)-1-hydroxyethyl>-1-methylcarbapen-2-em-3-carboxylate 
• 120410-24-4 biapenem 
• 141818-51-1 (4R,5S,6S)-3-((3S,5S)-1-Allyloxycarbonyl-5-dimethylcarbamoyl-pyrrolidin-3-ylsulfanyl)-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 138458-35-2 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[(3S,5S)-5-(4-methyl-piperazine-1-carbonyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 138401-02-2 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-4-methyl-3-[(3S,5R)-5-[2-(4-methyl-piperazin-1-yl)-2-oxo-ethyl]-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 138401-16-8 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(3S,5S)-5-[4-(2-hydroxy-ethyl)-piperazine-1-carbonyl]-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 138401-04-4 (4R,5S,6S)-6-((R)-1-Hydroxy-ethyl)-3-[(3S,5S)-5-[4-(2-methoxy-ethyl)-piperazine-1-carbonyl]-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 141818-66-8 (4R,5S,6S)-3-[(3S,5S)-5-{[(4,5-Bis-allyloxy-pyridine-2-carbonyl)-amino]-methyl}-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 
• 96036-02-1 p-nitrobenzyl (4R,5S,6S)-3-<(3S,5S)-5-dimethylaminocarbonyl-1-(p-nitrobenzyloxycarbonyl)pyrrolidin-3-ylthio>-6-<(1R)-1-hydroxyethyl>-4-methyl-7-oxo-1-azabicyclo<3.2.0>hept-2-en-2-carboxylate 
• 171009-53-3 (4R,5S,6S)-3-[(3S,5S)-5-(2-Carbamoyl-ethylsulfanylmethyl)-1-(4-nitro-benzyloxycarbonyl)-pyrrolidin-3-ylsulfanyl]-6-((R)-1-hydroxy-ethyl)-4-methyl-7-oxo-1-aza-bicyclo[3.2.0]hept-2-ene-2-carboxylic acid 4-nitro-benzyl ester 

Relevant articles and documents

PROCESS FOR THE PREPARATION OF CARBAPENEM COMPOUNDS

The present invention relates to a process for the preparation of carbapenem compound of Formula (I), wherein P1 is hydrogen or a carboxyl protecting group, P3 is hydrogen or a hydroxyl protecting group, R1 is C1-3 alkyl, and A is selected from a group consisting of a) Formula (II), b) Formula (III), c) Formula (IV), d) Formula (V), e) Formula (VI), f) Formula (VII), wherein P2 is hydrogen or an amino protecting group, R2 and R3 may be same or different and are hydrogen, C1-5 alkyl, optionally substituted aryl, or optionally substituted heteroaryl, and X1 is O or S, or its stereoisomers, or salts thereof.

AN IMPROVED PROCESS FOR THE PREPARATION OF MEROPENEM

The present invention provides an improved process for the preparation of methyl carbapenem derivative of formula (I) or its pharmaceutically acceptable salts or hydrates thereof in a pure form.

Improved process for the preparation of carbapenem using carbapenem intermediates and recovery of carbapenem

The present invention relates to preparing carbapenem intermediates that are useful to produce Ertapenem, Meropenem and Doripenem; and provides an effective process for recovering ertapenem compounds.

PROCESS FOR THE PREPARATION OF CARBAPENEM COMPOUNDS

The present invention relates to a process for the preparation of carbapenem compound of Formula (I), wherein P1 is hydrogen or a carboxyl protecting group, P3 is hydrogen or a hydroxyl protecting group, R1 is C1-3 alkyl, and A is selected from a group consisting of a) Formula (II), b) Formula (III), c) Formula (IV), d) Formula (V), e) Formula (VI), f) Formula (VII), wherein P2 is hydrogen or an amino protecting group, R2 and R3 may be same or different and are hydrogen, C1-5 alkyl, optionally substituted aryl, or optionally substituted heteroaryl, and X1 is O or S, or its stereoisomers, or salts thereof.

IMPROVED METHOD FOR THE CRYSTALLIZATION OF INTERMEDIATES OF CARBAPENEM ANTIBIOTICS

The present invention relates to an azetidinone compound extremely useful as a common intermediate for the synthesis of 1β-methylcarbapenem compounds. The present invention provides a crystallization method to obtain a crystal which has a higher quality and a higher stability than a conventional crystal and is excellent in filterability at the time of recovering crystal; an azetidinone compound having a low content of impurity; and an azetidinone compound which has a controlled particle size distribution of crystals and improved handleability and stability. The crystallization is carried out by adding a hydrocarbon solvent to a solution in which an azetidinone compound extremely useful as a common intermediate for the synthesis of 1β-methylcarbapenem compounds is dissolved in the presence of a seed crystal in an amount of 200% by weight or less based on the weight of the azetidinone compound. According to the method, the crystal having a high quality and a high stability and excellent filterability at the time of recovering the crystal can be obtained.

Process for The Preparation of Beta-Lactam Antibiotic

The present invention relates to a process for the preparation of Meropenem of formula (I) in sterile form and also provides an improved process for the preparation of compound of formula (V), which is an important intermediate in the synthesis of Meropenem.

A PROCESS FOR THE PREPARATION OF THE INTERMEDIATE OF Β-METHYL CARBAPENEM

A process of preparation of the intermediate of β-methyl carbapenem is disclosed, in which 4-acetylazacyclobutanone as the raw material is firstly reacted with α-bromopropionamide having a big inductive group. Since this reaction is highly stereoselectivity, most of the product is the required parent nucleus of β-methyl carbapenem, a product of β-configuration. Compared with the prior art, the process of the present invention is highly-yielding, cost-effective and can be used for large scale production.

AN IMPROVED PROCESS FOR THE PREPARATION OF BETA-LACTAM ANTIBIOTIC

The present invention relates to a process for the preparation of Meropenem of formula (I) in sterile form and also provides an improved process for the preparation of compound of formula (V), which is an important intermediate in the synthesis of Meropenem.

Synthesis and structure-activity relationships of 1β-methylcarbapenems with quaternary ammonium side chains

The synthesis and antibacterial activity of 1β-methylcarbapenems with quaternary ammonium groups at the C-2 position have been studied. Two types of new carbapenem derivatives have been synthesized. These 1β-methylcarbapenems, one type having a (2S,4S)-2-[1,1-dimethyl-2-(1-piperazinyl)carbonyl]pyrrolidinio-4-ylthio group and the other type having a (2S,4S)-2-(4-carbamoylmethyl-4-methylhomopiperazinio-1-ylcarbon-yl)pyrrolidin-4 -ylthio group, show potent and well balanced antibacterial activity as well as high stability against dehydropeptidase-I. The in vivo potency of these two carbapenems was compared with that of meropenem. The structure-activity relationships leading to these carbapenems are also described.

Studies on the synthesis and structure-activity relationships of 2-(2-functionalized pyrrolidin-4-ylthio)-1β-methylcarbapenems

A series of new carbapenem derivatives, which have a pyrrolidin-4-ylthio group substituted with a hydroxyalkyl or carbamoyl group at the 2′ position as the C-2 side chain, have been prepared. The antibacterial activity and the stability to renal dehydropeptidase-I of these compounds were investigated, and the structure-activity relationships were studied. Among these new carbapenems, (1R,5S,6S)-2-[(2S,4S)-2-{(2-hydroxy)ethylmercaptomethyl}pyrrolidin-4-ylthio]-6- [(1R)-1-hydroxyethyl]-1-methyl-1-carbapen-2-em-3-carboxylic acid (1a) showed the most potent and well balanced activity and was selected as a candidate for further evaluation.