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Usage

Uses

Used in Pharmaceutical Industry:
(4S)-4-Ethyl-2-oxazolidinone is used as a chiral building block for the preparation of chiral drugs and intermediates, playing a crucial role in the development of pharmaceuticals with specific stereochemistry for enhanced efficacy and safety.
Used in Organic Synthesis:
(4S)-4-Ethyl-2-oxazolidinone serves as a valuable reagent and solvent in various chemical reactions, particularly in asymmetric synthesis, enabling the creation of enantiomerically pure compounds for research and industrial applications.
Used in Antimicrobial Applications:
Due to its reported antimicrobial and antifungal properties, (4S)-4-ethyl-2-oxazolidinone is used as a potential candidate in the development of new antimicrobial agents, offering an alternative to conventional antibiotics and antifungal treatments.
Used in Chemical Research:
(4S)-4-Ethyl-2-oxazolidinone is utilized in chemical research for studying reaction mechanisms, exploring new synthetic routes, and developing innovative methodologies in organic chemistry.

InChI:InChI=1/C5H9NO2/c1-2-4-3-8-5(7)6-4/h4H,2-3H2,1H3,(H,6,7)/t4-/m0/s1

Upstream product

• 96-20-8 2-aminobutanol 
• 1659-31-0 2,2'-dipyridyl carbonate 
• 13997-20-1 4-ethyl-1,3-oxazolidine-2-thione 
• 592-35-8 butyl carbamate 
• 13973-23-4 2--1-butanol 
• 2549-67-9 2-ethylaziridine 
• 124-38-9 carbon dioxide 
• 468756-92-5 (4S,2'S,3'R)-N-(3-acetoxy-2-methylbutanoyl)-4-ethyl-2-oxazolidinone 
• 110418-29-6 (S)-(-)-2--1-butanol 
• 5856-62-2 (S)-2-aminobutan-1-ol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 928777-77-9 C₃₆H₅₃N₃O₃ 
• 124-41-4 sodium methylate 
• 616-38-6 carbonic acid dimethyl ester 

Downstream Products

• 5467-84-5 1,3-diphenethylurea 
• 1466-67-7 1,3-dibenzylurea 
• 100317-12-2 N-benzyl-N'-(1-hydroxymethyl-propyl)-urea 
• 6744-64-5 N,N'-dibenzhydryl-urea 
• 101785-47-1 N-benzhydryl-N'-(1-hydroxymethyl-propyl)-urea 
• 572923-07-0 4-ethyl-3-(4-methoxy-phenyl)-oxazolidin-2-one 
• 572923-15-0 2-((S)-4-Ethyl-2-oxo-oxazolidin-3-yl)-benzonitrile 
• 572923-13-8 4-(4-ethyl-2-oxo-oxazolidin-3-yl)-benzoic acid methyl ester 
• 572923-16-1 4-(4-ethyl-2-oxo-oxazolidin-3-yl)-N-propyl-benzamide 
• 909566-58-1 1-((S)-1-hydroxybutane-2-yl)pyrrolidin-2-one 
• 1269644-84-9 (S)-3-(3-(4-(1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one 
• 1269648-79-4 (S)-4-ethyl-3-(3-(4-(1-((2-(trimethylsilyl)ethoxy)methyl)-1H-1,2,4-triazol-3-yl)phenyl)pyrazolo[1,5-a]pyrimidin-5-yl)oxazolidin-2-one 
• 572922-98-6 4-(4-ethyl-2-oxo-oxazolidin-3-yl)-benzaldehyde 

Relevant academic research and scientific papers

Synchronized stereocontrol of planar chirality by crystallization-induced asymmetric transformation

Synchronized stereocontrol of two planar-chiral units was accomplished by using crystallization-induced asymmetric transformation (CIAT) of cyclophane-type bridged bisnicotinate derivatives 5b and 7. After screening various linkers, (S)-2-amino-1-butanol

A Rh-catalyzed C-H insertion reaction for the oxidative conversion of carbamates to oxazolidinones

Selective intramolecular alkane oxidations: an RhII carboxylate catalyzed C-H amination reaction facilitates the preparation of 1,2-amino alcohols from primary carbamates. The reaction is stereospecific, providing access to chiral α-branched amines from optically pure starting with no loss in enantiomeric excess (see scheme).

Efficient Access to Chiral 2-Oxazolidinones via Ni-Catalyzed Asymmetric Hydrogenation: Scope Study, Mechanistic Explanation, and Origin of Enantioselectivity

Cheap transition metal Ni-catalyzed asymmetric hydrogenation of 2-oxazolones was successfully developed, which provided an efficient synthetic strategy to prepare various chiral 2-oxazolidinones with 95%-99% yields and 97%->99% ee. The gram-scale hydrogenation could be proceeded well with >99% ee in the presence of low catalyst loading (up to 3350 TON). This Ni-catalyzed hydrogenation protocol demonstrated great synthetic utility, and the chiral 2-oxazolidinone product was easily converted to a variety of other important molecules in good yields and without loss of ee values, such as chiral dihydrothiophene-2(3H)-thione, amino alcohol, oxazoline ligand, and allenamide. Moreover, a series of deuterium labeling experiments, control experiments, and DFT calculations were conducted to illustrate a reasonable catalytic mechanism for this Ni-catalyzed asymmetric hydrogenation, which involved a tautomerization between the enamine and its isomer imine and then went through asymmetric 1,2-addition of Ni(II)-H to the preferred imine.

Preparation method of ethambutol

The invention relates to a preparation method of an antituberculosis drug ethambutol. The preparation method specifically comprises the following steps: a, reacting 2-amino-1 butanol with carbonic ester to generate a compound 2, b, reacting the compound 2 with dihalogenated ethane to generate a compound 3, and c, hydrolyzing the compound 3 to generate ethambutol. According to the preparation method of the ethambutol, the adopted raw materials are low in price and easy to obtain, and the method has the advantages of short synthetic route, novel route, high yield and no dangerous process.

COMBINATION TREATMENTS COMPRISING ADMINISTRATION OF 1H-PYRAZOLO[4,3-B]PYRIDINES

The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors together with a second compound which compound is useful in the treatment of a psychiatric disorder and their combined use as a medicament, in particular for the treatment of psychiatric and/or cognitive disorders.

COMBINATION TREATMENTS COMPRISING ADMINISTRATION OF 1H-PYRAZOLO[4,3-B]PYRIDINES

The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors together with a second compound useful in the treatment of a neurodegenerative disorder and their combined use as a medicament, in particular for the treatment of neurodegenerative and/or cognitive disorders.

1H-PYRAZOLO[4,3-B]PYRIDINES AS PDE1 INHIBITORS

The present invention provides 1H-pyrazolo[4,3-b]pyridin-7-amines of formula (I) as PDE1 inhibitors and their use as a medicament, in particular for the treatment of neurodegenerative disorders and psychiatric disorders.

Discovery and Evaluation of Clinical Candidate IDH305, a Brain Penetrant Mutant IDH1 Inhibitor

Inhibition of mutant IDH1 is being evaluated clinically as a promising treatment option for various cancers with hotspot mutation at Arg132. Having identified an allosteric, induced pocket of IDH1R132H, we have explored 3-pyrimidin-4-yl-oxazolidin-2-ones as mutant IDH1 inhibitors for in vivo modulation of 2-HG production and potential brain penetration. We report here optimization efforts toward the identification of clinical candidate IDH305 (13), a potent and selective mutant IDH1 inhibitor that has demonstrated brain exposure in rodents. Preclinical characterization of this compound exhibited in vivo correlation of 2-HG reduction and efficacy in a patient-derived IDH1 mutant xenograft tumor model. IDH305 (13) has progressed into human clinical trials for the treatment of cancers with IDH1 mutation.

Catalytic fluoride triggers dehydrative oxazolidinone synthesis from CO2

Herein, catalytic fluoride (F-) is demonstrated to be a trigger for dehydrative immobilization of atmospheric pressure CO2, such that reaction of CO2 with β-amino alcohols derived from natural amino acids gives optically pure oxazolidinones in high yields. A synergistic combination of fluoride and organosilicon agents (e.g., Bu4NF + Ph3SiF or siloxanes) enhances the catalytic activity and functional group compatibility. This system lies at the interface between homogenous and heterogeneous catalysis, and may prove useful for the development of recoverable/reusable siloxane-based CO2 immobilization materials. This journal is

Dehydrative synthesis of chiral oxazolidinones catalyzed by alkali metal carbonates under low pressure of CO2

Dehydrative synthesis of oxazolidinones from amino alcohols and CO 2 was achieved in the presence of alkali metal carbonates such as Cs2CO3 as catalyst. It is noteworthy that 1 atm of CO 2 is enough for the reaction to proceed and no special dehydrating agent is required in this system. A mechanstic study showed that the OH of amino alcohol acts as nucleophile and the OH in the carbamic acid moiety is liberated during the cyclization process.