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Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-benzyl-3-((2R,3R)-4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methylbutanoyl)oxazolidin-2-one is used as a synthetic intermediate for the development of complex molecules with biological activity. Its unique structure and chirality make it a promising candidate for the synthesis of pharmaceutical compounds with potential therapeutic applications.
Used in Chemical Synthesis:
In the field of chemical synthesis, (S)-4-benzyl-3-((2R,3R)-4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methylbutanoyl)oxazolidin-2-one serves as a versatile building block. Its precise stereochemistry and functional groups allow for the creation of a wide range of molecules with specific properties, making it an essential tool for researchers in organic chemistry.
Used in Research:
(S)-4-benzyl-3-((2R,3R)-4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methylbutanoyl)oxazolidin-2-one is utilized in research settings to explore its potential applications and properties. Its unique structure and chirality provide opportunities for studying the effects of stereochemistry on molecular interactions and reactivity, contributing to the advancement of scientific knowledge in the field of chemistry.

Upstream product

• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 51336-94-8 2-chloro-1-(2,4-dichlorophenyl)ethanone 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 192864-91-8 (4S)-4-benzyl-3-(2-bromopropanoyl)-1,3-oxazolidin-2-one 

Relevant academic research and scientific papers

Asymmetric zinc-Reformatsky reaction of Evans chiral imide with acetophenones and its application to the stereoselective synthesis of triazole antifungal agents

The Ni(acac)2 catalytic ZnEt2-mediated asymmetric Reformatsky-type reaction of Evans chiral imide with various acetophenones was studied. The chiral imido zinc enolate, which was formed through the metal-halogen exchange reaction of

Aldol condensation of Evans chiral enolates with acetophenones. Its application to the stereoselective synthesis of homochiral antifungal agents

The results of the aldol condensation of Evans chiral imide enolates with a series of acetophenones are reported. Activated acetophenones, such as 2,4-difluoroacetophenone, α-chloroacetophenone, and α-chloro- and α-bromo-2,4-difluoroacetophenone, reacted with the lithium enolate of 5 with good levels of enolate facial diastereoselectivity toward the (2R)-isomers (> 10:1) but with low anti: syn selectivity (ca. 3:2). Sodium and potassium enolates of 5 were also tested. The nature of the solvent influenced the degree of diastereofacial biases. Less activated ketones, such as acetophenone, reacted only to a ca. 50% extent without facial or anti:syn stereoselectivities. Chairlike pericyclic transition states are believed to govern the reaction. When α-bromoacetophenones were used, longer reaction times and higher temperatures resulted in the selective formation of the S2 epoxide (syn(2R,3R), 11) with good levels of selectivity. Equilibration studies performed in THF with the corresponding metal aldolates generated in situ by deprotonation of the aldol adducts indicated that an aldol/retroaldol process was first established followed by a slower formation of the epoxide. Stereoselection is thought to originate by a faster oxirane formation of the syn bromohydrins as compared to the anti due to steric interactions between the α-group and the leaving bromide. Optimum retroaldol-epoxide formation rates were obtained using the sodium enolate in ether at -78°C. Under these conditions the S1:S2:A1:A2 ratio of epoxides was 6:83:10:0.3 and the major isomer was isolated by recrystallization in 79% yield. An improved synthesis of amino alcohol 3, an advanced intermediate in the preparation of orally active antifungal agents, using a tandem of this new ketone-aldol technology and a Curtius rearrangement, is reported. The new sequence proceeds with an overall yield of 53% and does not require chromatographic purifications.