90822-24-5

Basic information

• Product Name: (F-9 (M-6))
• Synonyms: (F-9 (M-6));2-Azetidinebutanoic acid, α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-, (4-nitrophenyl)methyl ester, (γR,2R,3S)-
• CAS NO: 90822-24-5
• Molecular Formula: C₁₇H₁₈N₄O₇
• Molecular Weight: 594.5
• Mol File: 90822-24-5.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (F-9 (M-6))(CAS DataBase Reference)
• NIST Chemistry Reference: (F-9 (M-6))(90822-24-5)
• EPA Substance Registry System: (F-9 (M-6))(90822-24-5)

Safety Data

• Hazardous Substances Data: 90822-24-5(Hazardous Substances Data)

Usage

Uses

4-Nitrobenzyl (R)-2-diazo-4-((2R,3S)-3-((R)-1-hydroxyethyl)-4-oxoazetidin-2-yl)-3-oxopentanoate is used as a reactant in the preparation of carbapenem compounds for treatment of bacterial infections. It is also the impurity of Meropenem (M225668), which is an ultra-broad spectrum injectable antibiotic used to treat a wide variety of infections, including meningitis and pneumonia.

Upstream product

• 90822-23-4 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one 
• 102832-08-6 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<((4S)-4-isopropyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one 
• 109267-65-4 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-<((4S)-4-ethyl-2-thioxo-1,3-thiazolidin-3-yl)carbonyl>ethyl>azetidin-2-one 
• 124667-64-7 (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-[(R)-2-imidazol-1-yl-1-methyl-2-oxoethyl]azetidin-2-one 
• 105995-50-4 magnesium 4-nitrobenzyl malonate 
• 76899-07-5 (3R,4R)-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]-4-acetoxyazetidin-2-one 
• 86420-90-8 (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-methoxycarbonylmethyl-azetidin-2-one 
• 90776-57-1 (3S,4R)-3-<(1R)-1-formyloxyethyl>-4-methoxycarbonylmethyl-azetidin-2-one 
• 90822-22-3 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>azetidin-2-one 
• 87037-97-6 methyl (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionate 
• 87037-96-5 (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-(methoxycarbonyl)ethyl>azetidin-2-one 
• 185446-92-8 (3S,4R)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(methoxycarbonyl)methyl>azetidin-2-one 
• 79779-57-0 (3S,4R)-3-<(1S)-1-hydroxyethyl>-4-methoxycarbonylmethyl-azetidin-2-one 
• 93711-85-4 (2R)-2-[(2S,3S)-3-{(1R)-1-(t-butyldimethylsilyloxy)ethyl}-4-oxoazetidin-2-yl]propionic acid 

Downstream Products

• 127767-59-3 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(2-fluoroethyloxymethyl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-59-5 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(1,2,4-oxadiazol-5-yl)pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-60-8 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-{2-(ureidomethyl)thiazol-4-yl}pyrrolidin-4-yl]thio-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-27-7 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(1,3-dioxolan-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-32-4 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-2-(1H-tetrazol-5-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-7-oxo-1azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-47-1 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-{2-(carbamoyloxymethyl)thiazol-4-yl}-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-48-2 4-Nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(3-amino-1,2,4-oxadiazol-5-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-51-7 4-nitrobenzyl (4R,5S,6S)-3-[(2S,4S)-2-(4-carbamoylthiazol-2-yl)-1-(4-nitrobenzyloxycarbonyl)pyrrolidin-4-yl]thio-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-49-3 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[3-{N-(4-nitrobenzyloxycarbonyl)aminomethyl]-1,2,4-oxadiazol-5-yl]pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylate 
• 117334-50-6 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-[3-{N-(4-nitrobenzyloxycarbonyl)aminomethyl}-1H-1,2,4-triazol-5-yl]pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 117334-21-1 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-(2-thiazolin-2-yl)pyrrolidin-4-ylthio]-7-oxo-1-azabicyclo-[3.2.0]hept-2-ene-2-carboxylate 
• 117334-23-3 4-Nitrobenzyl (4R,5S,6S)-6-[(1R)-1-hydroxyethyl]-4-methyl-3-[(2S,4S)-1-(4-nitrobenzyloxycarbonyl)-2-{1-(4-nitrobenzyloxycarbonyl)-2-imidazolin-2-yl}-pyrrolidin-4-yl]thio-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 

Relevant articles and documents

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.

A PROCESS FOR THE PREPARATION OF MEROPENEM

The invention relates to a process for the preparation of meropenem, a β-methylcarbopenem. The said process comprises the following steps: preparing the compound of Formula (XI) from the compound of Formula (IV) through three steps "one-pot process"; then condensing the compound of Formula (XI) with the compound of Formula (XX) to form the compound of Formula (XXIV); finally preparing meropenam of Formula (I) from the compound of Formula (XXIV) by deprotection reaction by means of catalyst. The process of the invention is easily to carry out, the product is isolated in high content and yield, and the cost is reduced, thereby overcoming the shortage of the prior art.

SYNTHETIC CARBAPENEM ANTIBIOTICS I. 1-&β-METHYLCARBAPENEM

A total synthesis of a novel 1-β-methylcarbapenem antibiotic, (-)-(1R,5S,6S)-2-(2-N,N-dimethylamino-2-iminoethylthio)-6--1-methylcarbapen-2-em-3-carboxylic acid 1, is reported.Compound 1 is highly resistant to renal dipeptidase-I yet retains the excellent antibacterial activities of N-formimidoylthienamycin.