90822-24-5

Usage

Uses

Used in Pharmaceutical Industry:
(F-9 (M-6)) is used as a reactant for the synthesis of carbapenem compounds, which are a class of antibiotics with potent antibacterial activity. These compounds are effective against a wide range of bacterial infections, including those caused by gram-negative and gram-positive bacteria, as well as anaerobic bacteria.
Additionally, (F-9 (M-6)) is identified as an impurity in Meropenem (M225668), an ultra-broad-spectrum injectable antibiotic. Meropenem is used to treat a variety of infections, such as meningitis and pneumonia, due to its effectiveness against a wide range of bacteria. The presence of (F-9 (M-6)) as an impurity in Meropenem highlights the importance of monitoring and controlling the quality of pharmaceutical products to ensure their safety and efficacy.

Upstream product

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

Downstream Products

• 90822-25-6 p-nitrobenzyl (1R,5S,6S)-6-<(R)-1-hydroxyethyl>-1-methyl-2-oxo-carbapanem-3-carboxylate 
• 165817-82-3 4-nitrobenzyl (1R,5R,6S)-1-methyl-6-[(1R)-triethylsilanyloxy-ethyl]-2-(trifluoro-methanesulfonyloxy)-carbapen-2-em-3-carboxylate 
• 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 

Relevant academic research and scientific papers

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 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.

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.

β-Lactams. 3. Asymmetric Total Syntheis of New Non-Natural 1β-Methylcarbapenems Exhibiting Strong Antimicrobial Activities and Stability against Human Renal Dehydropeptidase-I

Asymmetric synthesis of 11, the precursor to chiral (3R,4R)-3-ethyl>-4-acetoxyazetidin-2-one (3) was achieved by utilizing a highly diastereoselective aldol-type reaction of acetaldehyde and the chiral tin(II) enolate of 5.Similar diastereoselective alkylations of chiral and achiral tin(II) enolates 13a-d with chiral 3 were also performed to obtain the desired alkylated azetidin-2-ones (17a-d).Compounds 17a,b were successfully converted to new, non-natural 1β-methylcarbapenems 1a and 1b, which exhibited strong and wide-ranging antimicrobial activities and excellent stability against human renal dehydropeptidase-I.

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.