160695-26-1

Usage

Uses

Used in Medical Applications:
(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is used as an antimicrobial agent for treating a variety of infections, particularly those that are resistant to other antibiotics. Its application in this context is due to the compound's inherent antimicrobial properties, which make it a valuable tool in the medical field for combating antibiotic-resistant infections.
Used in Pharmaceutical Development:
In the pharmaceutical industry, (R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is used as a potential candidate for the development of new drugs. Its unique structure and antimicrobial activity make it a promising starting point for the creation of novel therapeutics that could address the growing challenge of antibiotic resistance.
Used in Research and Development:
(R)-4-PHENYL-3-PROPIONYL-2-OXAZOLIDINONE is also utilized in research settings to study its chemical properties, potential interactions with biological systems, and its effectiveness against specific types of infections. This research can lead to a better understanding of the compound's capabilities and limitations, as well as inform the development of new formulations or applications.

InChI:InChI=1/C12H13NO3/c1-2-11(14)13-10(8-16-12(13)15)9-6-4-3-5-7-9/h3-7,10H,2,8H2,1H3/t10-/m0/s1

Upstream product

• 79-03-8 propionyl chloride 
• 120666-53-7 (R)-benzyl [2-hydroxy-1-phenylethyl]carbamate 
• 201300-96-1 (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one 
• 100-52-7 benzaldehyde 
• 90319-52-1 (4R)-phenyl-2-oxazolidinone 
• 123-62-6 propionic acid anhydride 
• 124-38-9 carbon dioxide 
• 186581-53-3 diazomethane 
• 86217-38-1 4-phenyl-2-oxazolidinone 
• 56613-80-0 D-2-phenylglycinol 
• 802294-64-0 propionic acid 

Downstream Products

• 439278-07-6 (R)-4-phenyl-3-((2R,3S)-3-hydroxy-2-methylnonanoyl)-1,3-oxazolidin-2-one 
• 439278-12-3 (R)-4-phenyl-3-((2R,3S)-3-hydroxy-2-methyloctanoyl)-1,3-oxazolidin-2-one 
• 615579-48-1 (4R)-4-phenyl-3-(1S)-1-[(trimethylsilyl)oxy]propyl-1,3-oxazolan-2-one 
• 900807-41-2 (R)-3-[(2R,3S)-3-Hydroxy-2-methyl-5-((4S,6S)-2,2,6-trimethyl-[1,3]dioxan-4-yl)-pentanoyl]-4-phenyl-oxazolidin-2-one 
• 1314641-25-2 (R)-3-((S)-2-methylpent-4-enoyl)-4-phenyloxazolidin-2-one 
• 1335544-75-6 (4R)-4-phenyl-3-[(2R)-3,3,3-trifluoro-2-methylpropanoyl]-1,3-oxazolidin-2-one 
• 114418-61-0 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-((R)-4-phenyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 1258861-66-3 (4R)-3-[(2R,3S)-3-hydroxy-2-methylpent-4-enoyl]-4-phenyl-oxazolidin-2-one 

Relevant academic research and scientific papers

Diastereoselective Electrochemical Carboxylation of Chiral α-Bromocarboxylic Acid Derivatives: An Easy Access to Unsymmetrical Alkylmalonic Ester Derivatives

The diastereoselective electrochemical carboxylation of chiral N-(2-bromoacyl)oxazolidin-2-ones has been studied. This reaction was carried out by cathodic reduction of the C - Br bond, in the presence of carbon dioxide, followed by treatment with diazomethane. The yields and the diastereomeric ratio of the two epimeric alkylmalonic acid derivatives are strongly affected by various factors: solvent-supporting electrolyte system, temperature, electrode material, electrolysis conditions, oxazolidinone moiety. The higher yields (88%) were obtained starting from N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one la, but with poor diastereoselectivity (61:39). The two epimers were easily separated by flash chromatography. The best results were achieved using a different chiral auxiliary: Oppolzer's camphor sultam. Starting from 1j a good yield in carboxylated product was obtained (80%) with excellent diastereoselectivity (98:2). These chiral alkylmalonic acid derivatives are valuable building blocks in the synthesis of molecules with biological activity and of chiral propane-1,3-diols derivatives.

Total synthesis of natural (?)- and unnatural (+)-Melearoride A

This communication details the first total synthesis of the 13-membered macrolide, (?)-Melearoride A, as well as unnatural (+)-Melearoride A. The synthesis features a concise 13 step synthesis (11 steps longest linear sequence) that offers flexible stereo-control and multiple opportunities for unnatural analog synthesis to delve into antifungal SAR. The route features a cuprate addition, an Evans asymmetric alkylation, and a ring-closing metathesis (RCM) to close the 13-membered macrocyclic core.

Diastereoselective Electrophilic Trifluoromethylthiolation of Chiral Oxazolidinones: Access to Enantiopure α-SCF3 Alcohols

Lithium imide enolates featuring Evans’ chiral oxazolidinone auxiliary were involved in diastereoselective α-trifluoromethylthiolation with electrophilic SCF3 donors. Diastereopure products were isolated and converted to enantiopure α-SCF3 alcohols without racemisation. (Figure presented.).

AHU - 377 preparation method of the midbody and intermediate and intermediate preparation method

The invention relates to the field of chemical synthesis of medicines and in particular relates to a preparation method and intermediate of an AHU-377 intermediate and a preparation method of the intermediate. The preparation method of the AHU-377 intermediate shown in a formula (I) in the description comprises the following steps: performing a substitution reaction on a compound shown in a formula (II) in the description and a compound shown in a formula (III) in the description and then carrying out hydrolysis to prepare the AHU-377 intermediate shown in the formula (I), wherein the hydrolysis reaction is carried out in the presence of hydrogen peroxide and lithium hydroxide hydrate. The invention also aims to provide a new compound with a structure shown in the formula (II). In the new route, as a new compound shown in a formula (IV) in the description is prepared through reaction of the compound in the formula (II) and the compound in the formula (III), the selectivity is quite good, and a few diastereoisomers are generated in the reaction process and can be removed only through simple aftertreatment.

PROCESS FOR THE PREPARATION OF (1S,3S,7S,10R,11S,12S,16R)-7,11-DIHYDROXY-8,8,10,12,16-PENTAMETHYL-3-[(1E)-1-METHYL-2-(2-METHYL-4-THIAZOLYL)ETHENYL]-17-OXA-4-AZABICYCLO[14.1.0]HEPTADECANE-5,9-DIONE AND INTERMEDIATES THEREOF

The present invention relates to an improved process for the preparation of (1S,3S,7S,10R,11S,12S,16R)-7,11-dihydroxy-8,8,10,12,16-pentamethyl-3-[(1E)-1-methyl-2-(2- methyl-4-thiazolyl)ethenyl]- 17-oxa-4-azabicyclo[ 14.1.0]heptadecane-5,9-dione represented by the following structural formula I and intermediates thereof. The present invention also provides novel intermediate compounds useful for the preparation of compound of formula I and its intermediates.

Absolute configuration of lactams and oxazolidinones using kinetic resolution catalysts

A simple method for determining the absolute configuration of oxazolidinones, lactams, and their derivatives using kinetic resolution catalysts is described. The optically pure substrates were acylated using the (S)-HBTM and the (R)-HBTM catalyst, and the faster reaction was determined. An empirical mnemonic was developed for the assignment of the absolute configuration based on the fast-reacting catalyst.

Synthesis of α-CF3-substituted carbonyl compounds with relative and absolute stereocontrol using electrophilic CF3-transfer reagents

Evans-type chiral lithium imide enolates undergo diastereoselective α-trifluoromethylation with a hypervalent iodine-CF3 reagent with up to 91% combined isolated yield and 97:3 dr. The resulting isolated diastereopure products can be further transformed into valuable products without racemization.

Kinetic resolution of 2-oxazolidinones via catalytic, enantioselective N-acylation

Kinetic resolution of racemic 2-oxazolidinones via catalytic, enantioselective N-acylation has been achieved for the first time and with outstanding selectivities. Copyright

Development of a scalable process for 1-β-methyl azetidinone: A carbapenem key intermediate

An optimized process for the stereoselective synthesis of 1-β-methyl carbapenem key intermediate (3S,4S)-[(R)-1′-((tert-butyldimethylsilyl)oxy) ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone (1) and (3R,4R)-4-acetoxy-3-[(R)- 1′-((tert-butyldimethylsilyl)oxy)ethyl]-2-azetidinone has been developed employing commercially available chiral 4-phenyl-2-oxazolidinone. This method provides an efficient and cost-effective process with improved selectivity and higher yield.

Electrochemical carboxylation of N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one: An efficient route to unsymmetrical methylmalonic ester derivatives

(Matrix presented) Electrochemical carboxylation of N-(2-bromopropionyl)-4R-phenyloxazolidin-2-one aimed at the synthesis and chiral resolution of unsymmetrical methylmalonic ester derivatives is described. The presence of the Evans' chiral auxiliary perm