90822-23-4

Usage

Uses

Used in Pharmaceutical Industry:
(3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one is used as a pharmaceutical intermediate for the synthesis of complex drug molecules. Its unique structure and functional groups allow for the development of new therapeutic agents with potential applications in treating various diseases.
Used in Organic Synthesis:
In the field of organic synthesis, (3S,4R)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-p-nitrobenzyloxycarbonyl-2-oxopropyl>-2-azetidin-2-one serves as a key building block for the creation of more complex organic compounds. Its versatile functional groups enable chemists to perform a range of reactions, leading to the formation of novel molecules with potential applications in various industries, such as materials science, agrochemicals, and specialty chemicals.

Upstream product

• 97101-07-0 (3S,4S)-3-<(1R)-1-<(tert-Butyldimethylsilyl)oxy>ethyl>-4-<(1S)-1-carboxyethyl>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 
• 93576-40-0 (3S,4R)-1-(tert-Butyldimethylsilyl)-3-<(1R)-1-hydroxyethyl>-4-<(1R)-1-methyl-3-(p-nitrobenzyloxycarbonyl)-2-oxopropyl>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 
• 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 
• 102832-02-0 (4S)-4-<(1R)-1-carboxyethyl>-1-(tert-butyldimethylsilyl)-2-oxoazetidine 
• 102832-04-2 (3S,4S)-3-Acetyl-1-(tert-butyldimethylsilyl)-4-<(1R)-1-carboxyethyl>azetidin-2-one 

Downstream Products

• 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 
• 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 
• 93711-81-0 (4-nitrophenyl)methyl (4R,5R,6S)-3-[(diphenoxyphosphinyl)oxy]-6-[(1R)-1-hydroxyethyl]-4-methyl-7-oxo-1-azabicyclo[3.2.0]hept-2-ene-2-carboxylate 
• 96036-03-2 meropenem 
• 90822-24-5 (γR,2R,3S)-α-diazo-3-[(1R)-1-hydroxyethyl]-γ-methyl-β,4-dioxo-2-azetidinebutanoic acid (4-nitrophenyl)methyl ester 

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 III. 1-Methyl thienamycin

Total syntheses of 1α- and 1β-methyl thienamycin are reported. 1β-Methyl thienamycin retains the antibacterial activity of thienamycin and is highly resistant to hydrolysis by HPD-1 enzyme.

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.