99333-54-7

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(+)-2-Oxo-4-phenyl-3-oxazolidineacetic acid is used as a chiral building block for the synthesis of chiral β-lactams via the Staudinger reaction. These β-lactams are important components in the development of antibiotics and other pharmaceuticals, as they exhibit potent antimicrobial and antibacterial properties.
Used in Organic Synthesis:
(S)-(+)-2-Oxo-4-phenyl-3-oxazolidineacetic acid is used as a chiral synthon for the preparation of unnatural dipeptides. The chiral ketene derived from this product allows for the creation of complex peptide structures with specific stereochemistry, which can be crucial for the biological activity and selectivity of peptide-based drugs.

InChI:InChI=1/C11H11NO4/c13-10(14)6-12-9(7-16-11(12)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)/t9-/m1/s1

Upstream product

• 99333-53-6 ethyl 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetate 
• 108493-65-8 (S)-ethyl (2-hydroxy-1-phenylethyl)carbamate 
• 105-36-2 ethyl bromoacetate 
• 910322-90-6 (2-oxo-(4S)-phenyloxazolidin-3-yl) acetic acid benzyl ester 
• 20989-17-7 (2S)-2-phenylglycinol 
• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 60729-80-8 (S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid 
• 2935-35-5 (S)-2-phenylglycine 

Downstream Products

• 218290-86-9 (S)-2-[(2R,3S)-2-(2-Bromo-phenyl)-4-oxo-3-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-azetidin-1-yl]-propionic acid methyl ester 
• 99333-59-2 (S)-3-((3S,4R)-1-Benzyl-2-oxo-4-phenyl-azetidin-3-yl)-4-phenyl-oxazolidin-2-one 
• 182321-22-8 (+)-(3S,4R)-1-(2-bromophenyl)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-4-(E)-1-propenyl-azetidin-2-one 
• 182321-19-3 (+)-(3S,4R)-1-(2-bromophenyl)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-4-(E)-styryl-azetidin-2-one 
• 850478-80-7 (+)-(3S,4R)-1-(2-bromobenzyl)-3-[(S)-4-phenyl-2-oxo-1,3-oxazolidin-3-yl]-4-(E)-styryl-azetidin-2-one 
• 139731-96-7 methyl (4(S)-phenyloxazolidin-2-on-3-yl)acetate 
• 99333-55-8 2-(4(S)-phenyloxazolidin-2-on-3-yl)acetyl chloride 
• 244248-96-2 (4S,5R,6S)-4-Benzyl-3-[1-diphenylphosphanyl-meth-(Z)-ylidene]-6-((S)-2-oxo-4-phenyl-oxazolidin-3-yl)-1-aza-bicyclo[3.2.0]heptan-7-one 
• 850355-12-3 methyl 2-(4(S)-phenyloxazolidin-2-on-3-yl)propanoate 
• 1432500-66-7 (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl)methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid 
• 1607007-22-6 (S)-(2-benzyl-1,2,3,4-tetrahydroisoquinolin-1-yl)methanol 
• 1607007-23-7 2-{[(1S)-2-benzyl-1,2,3,4-tetrahydroisoquinolin-1-yl]methyl}-2,3-dihydro-1H-isoindole-1,3-dione 

Relevant academic research and scientific papers

Deconstructing Noncovalent Kelch-like ECH-Associated Protein 1 (Keap1) Inhibitors into Fragments to Reconstruct New Potent Compounds

Targeting the protein-protein interaction (PPI) between nuclear factor erythroid 2-related factor 2 (Nrf2) and Kelch-like ECH-associated protein 1 (Keap1) is a potential therapeutic strategy to control diseases involving oxidative stress. Here, six classes of known small-molecule Keap1-Nrf2 PPI inhibitors were dissected into 77 fragments in a fragment-based deconstruction reconstruction (FBDR) study and tested in four orthogonal assays. This gave 17 fragment hits of which six were shown by X-ray crystallography to bind in the Keap1 Kelch binding pocket. Two hits were merged into compound 8 with a 220-380-fold stronger affinity (Ki = 16 μM) relative to the parent fragments. Systematic optimization resulted in several novel analogues with Ki values of 0.04-0.5 μM, binding modes determined by X-ray crystallography, and enhanced microsomal stability. This demonstrates how FBDR can be used to find new fragment hits, elucidate important ligand-protein interactions, and identify new potent inhibitors of the Keap1-Nrf2 PPI.

Synthetic method for aztreonam mother nucleus

The invention provides a synthetic method for an aztreonam mother nucleus. The method uses sulfamic acid and ethyl bromoacetate as starting raw materials and produces the aztreonam mother nucleus through a chiral prosthetic group-induced 2+2 addition reaction. The method has the advantages of low price of raw materials and high yield, and does not use the high-risk chemical chlorosulfonic acid.

Binding mode and structure-activity relationships around direct inhibitors of the Nrf2-Keap1 complex

An X-ray crystal structure of Kelch-like ECH-associated protein (Keap1) co-crystallised with (1S,2R)-2-[(1S)-1-[(1,3-dioxo-2,3-dihydro-1H-isoindol-2-yl) methyl]-1,2,3,4-tetrahydroisoquinolin-2-carbonyl]cyclohexane-1-carboxylic acid (compound (S,R,S)-1 a) was obtained. This X-ray crystal structure provides breakthrough experimental evidence for the true binding mode of the hit compound (S,R,S)-1 a, as the ligand orientation was found to differ from that of the initial docking model, which was available at the start of the project. Crystallographic elucidation of this binding mode helped to focus and drive the drug design process more effectively and efficiently. To dock or not to dock? Nrf2 has become an attractive neuroprotective target, as the Nrf2 pathway provides a natural cell defense mechanism against damage. Targeting its physiological negative modulator Keap1 with small molecules may allow Nrf2 to play its protective role. To this end, an X-ray structure of Keap1 co-crystallised with compound (S,R,S)-1 a was obtained, elucidating its binding mode, which in turn helped to drive the drug design process.

Ramoplanin derivatives possessing antibacterial activity

Novel ramoplanin derivatives are disclosed. These ramoplanin derivatives exhibit antibacterial activity. As the compounds of the subject invention exhibit potent activities against gram positive bacteria, they are useful antimicrobial agents. Methods of synthesis and of use of the compounds are also disclosed.

Diastereoselective [4+3] cycloadditions of enantiopure nitrogen-stabilized oxyallyl cations

Diastereoselective trapping of chiral enantiopure oxyallyl cations by common dienes is reported. Excellent diastereoselectivities were obtained and depending on which auxiliary was used cycloadditions proceeded through a chelated or non-chelated pathway.

AN ENANTIOSELECTIVE SYNTHESIS OF LORACARBEF (LY163892/KT3777)

An enantioselective synthesis of the new, orally absorbable, totally synthetic β-lactam antibiotic, loracarbef(LY163892/KT3777) is described.

Process and intermediates for β-lactam antibiotics

1-Benzyl (or substituted benzyl)-3β-[4(S)-aryloxazolidin-2-one-3-yl]-4β-(2-arylvinyl)azetidin-2-ones are provided via cycloaddition of a 4(S)-aryloxazolidin-2-one-3-ylacetyl halide and an imine formed with a benzylamine and a 3-arylacrolein, e.g. cinnamaldehyde. The azetidinones are useful chiral intermediates in an asymmetric synthesis of 1-carba(1-dethia)-3-hydroxy-3-cephem-4-carboxylic acids and esters and to monocyclic β-lactam antibiotics.

7-acylamino-(or 7-amino)-3-trifluoromethylsulfonyloxy-1-carba(1-dethia)-3-cephem-4-carboxylic acids and esters thereof

7β-Acylamino-3-trifluoromethylsulfonyloxy-1-carba-3-cephem-4-carboxylic acid antibiotic compounds, esters and salts thereof, and the corresponding 7-amino and protected 7-amino 1-carbacephalosporins are provided. The 3-trifluoromethylsulfonyloxy-substituted 1-carbacephalosporins also are useful in a process for preparing 3-halo-1-carbacephalosporins which comprises reacting a 3-triflate ester with a lithium halide in an aprotic polar solvent.

The asymmetric synthesis of β-lactam antibiotics. I. Application of chiral oxazolidones in the Staudinger Reaction

The reactions of oxazolidone with N-benzylimines proceed with exceptional levels of asymmetric induction to form the cycloadducts. Subsequent dissolving metal reduction affords the homochiral β-lactam derivatives in good overall yield.