150895-72-0

Basic information

• Product Name: 4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone
• Synonyms: 4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone
• CAS NO: 150895-72-0
• Molecular Weight: 284.109
• Mol File: 150895-72-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: 4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone(150895-72-0)
• EPA Substance Registry System: 4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone(150895-72-0)

Safety Data

• Hazardous Substances Data: 150895-72-0(Hazardous Substances Data)

Upstream product

• 99395-88-7 (S)-4-phenyl-2-oxazolidinone 
• 598-21-0 2-Bromoacetyl bromide 
• 22118-09-8 2-bromoacetyl chloride 

Downstream Products

• 1243256-60-1 (S)-dimethyl [2-oxo-2-(2-oxo-4-phenyloxazolidin-3-yl)ethyl]phosphonate 
• 218782-69-5 (S)-3-{(E)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-acryloyl}-4-phenyl-oxazolidin-2-one 
• 201340-11-6 (S)-3-{(S)-3-[2-((E)-(R)-4-Bromo-2-triisopropylsilanyloxy-pent-3-enyl)-thiazol-4-yl]-butyryl}-4-phenyl-oxazolidin-2-one 
• 201340-02-5 (4S)-3-[(diethylphosphoro)-acetyl]-4-phenyl-2-oxazolidinone 

Relevant articles and documents

Synthesis of enantioenriched α-chiral bicyclo[1.1.1]pentanes

Bicyclo[1.1.1]pentanes (BCPs), useful surrogates for para-substituted arenes, alkynes, and tert-butyl groups in medicinal chemistry, are challenging to prepare when featuring stereogenic centers adjacent to the BCP. We report the development of an efficie

Asymmetric Samarium-Reformatsky Reaction of Chiral α-Bromoacetyl-2-oxazolidinones with Aldehydes

The samarium(II) iodide mediated asymmetric Reformatsky-type reaction of chiral 3-bromoacetyl-2-oxazolidinones with various aldehydes was studied. A series of chiral 4-substituted 2-oxazolidinones 1-3 and 5,5-disubstituted "SuperQuat" oxazolidinones 4-5 were employed as chiral auxiliaries of the α-bromoacetic acid. The reaction of 1 with various aldehydes gave the α-unbranched β-hydroxy carboximides in good yields with high diastereomeric excess values (up to >99% de). The majority of the reaction product derived from 5,5-diphenyl SuperQuat 5 were highly crystallinity; a single recrystallization yielding a diastereomerically pure product with the other diastereomer not detectable by spectroscopic methods. The absolute configurations of the β-hydroxy carboximides were determined by signs of optical rotations of the corresponding known ethyl esters referring to the literature values. Hydrolytic cleavage of the appended of β-hydroxy moieties from the auxiliary SuperQuats was readily achieved under mild conditions using lithium hydroxide; the corresponding carboxylic acids and the returned SuperQuats were obtained in good yields without any evidence of racemization. The first step of the reaction is the reduction of the α-bromo group to produce the samarium enolate, which adds to an aldehyde. The absolute configuration of the adduct (7i) derive from benzaldehyde was found to be R, with the samarium enolate favoring the transition state predicted from chelation control of the reagent; this is in analogy to the discussion that has been used for the corresponding titanium enolate. The stereochemistry of the reaction may be explained by incorporating the Nerz-Stormes-Thornton chair transition structure model.