192864-91-8

Basic information

• Product Name: (4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one
• Synonyms: (4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one;(4S)-3-(2-Bromo-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS NO: 192864-91-8
• Molecular Formula: C₁₃H₁₄BrNO₃
• Molecular Weight: 312.16
• Mol File: 192864-91-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 429.956 °C at 760 mmHg
• Flash Point: 213.83 °C
• Appearance: /
• Density: 1.508
• CAS DataBase Reference: (4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one(192864-91-8)
• EPA Substance Registry System: (4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one(192864-91-8)

Safety Data

• Hazardous Substances Data: 192864-91-8(Hazardous Substances Data)

Usage

Description

(4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one, also known as BPO, is a chemical compound with the molecular formula C14H15BrNO3. It is an oxazolidinone derivative that contains a 2-bromopropanoyl group and a benzyl group attached to the oxazolidin-2-one ring. BPO is a versatile building block for the synthesis of various pharmaceuticals and biologically active compounds due to its unique structure and functional groups. It is commonly used as an intermediate in organic synthesis and pharmaceutical research, and its potential biological activities make it a valuable molecule for drug discovery and development.

Uses

Used in Pharmaceutical Research:
(4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one is used as an intermediate in pharmaceutical research for the development of new drugs. Its unique structure and functional groups allow for the synthesis of a wide range of biologically active compounds, making it a valuable asset in the field of medicinal chemistry.
Used in Organic Synthesis:
(4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one is used as a versatile building block in organic synthesis. Its 2-bromopropanoyl and benzyl groups can be utilized to create a variety of chemical compounds, contributing to the diversity of molecules that can be synthesized.
Used in Drug Discovery:
(4S)-4-benzyl-3-(2-bromopropanoyl)oxazolidin-2-one is used as a valuable molecule in drug discovery due to its potential biological activities. Its unique structure and functional groups make it an attractive candidate for the development of new pharmaceuticals with various therapeutic applications.

Upstream product

• 201300-96-1 (4'R)-2-bromo-1-(2'-oxo-4'-phenyloxazolidin-3'-yl)propan-1-one 
• 75-61-6 dibromodifluoromethane 
• 131685-53-5 (S)-4-benzyl-3-propionyl-2-oxazolidinone 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 563-76-8 α-bromopropionyl bromide 

Downstream Products

• 1204590-45-3 (4S,2'R,3'R)-3-(3'-hydroxy-2'-methylhexanoyl)-4-benzyl-2-oxazolidinone 
• 1204590-44-2 (4S,2'R,3'S)-3-(3'-hydroxy-2'-methylhexanoyl)-4-benzyl-2-oxazolidinone 
• 169218-76-2 (4S)-4-benzyl-3-[(2S)-4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl]-1,3-oxazolidin-2-one 
• 169218-76-2 <3(2R,3S),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 169218-76-2 <3(2R,3R),4S>-4-Benzyl-3-<4-chloro-3-(2,4-difluorophenyl)-3-hydroxy-2-methyl-1-oxobutyl>-2-oxazolidinone 
• 133467-37-5 (4S)-3-[(2S,3S)-3-hydroxy-2-methyl-3-phenylpropanoyl]-4-benzyl-2-oxazolidinone 
• 131899-77-9 (4S)-3-[(2R,3R)-2,4-dimethyl-3-hydroxy-1-oxo-1-pentyl]-4-phenylmethyl-1,3-oxazolidin-2-one 
• 109616-59-3 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(S)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 
• 109715-77-7 (3S,4R)-3-<(R)-1-(t-Butyldimethylsilyloxy)ethyl>-4-<(R)-1-((S)-4-benzyl-2-oxazolidone-3-carbonyl)ethyl>-2-azetidinone 

Relevant articles and documents

Diastereoselective bromodifluoromethylation of chiral imide enolates via insertion of difluorocarbene

The bromodifluoromethylation of lithium enolates of chiral N-acyloxazolidinones via the insertion of difluorocarbene proceeds with good diastereomeric excess (68-92% de).

An Activated Germanium Metal-Promoted, Highly Diastereoselective Reformatsky Reaction

Activated germanium metal, prepared by the reduction of germanium(II) iodide with potassium metal, was found to promote the Reformatsky reaction effectively under mild conditions. In the presence of activated germanium metal, the reactions of α-bromo ketones 2a and 2b and α-bromo imides 2e and 2f with benzaldehyde (1a) proceeded smoothly to give the corresponding β-hydroxy carbonyl compounds 3a, 3b, 3e and 3f, respectively, in good yields and with good syn diastereo- selectivity. The activated germanium metal-promoted, asymmetric Reformatsky reaction of enantiomerically pure-oxazolidinone derivatives 2g-j with various aldehydes 1a-d was also examined; the highest diastereoselectivity was achieved when (1S,2R)-2-amino-1,2-diphenylethanol- derived 2j was used as the Reformatsky donor. The excellent diastereoselectivity could be explained in terms of the formation of a chairlike, six-membered transition state between the aldehyde and enolate as in the Zimmerman-Traxler model. A single recrystallization of the Reformatsky adducts, followed by hydrolysis and subsequent esterification, led to enantiomerically pure methyl 3-hydroxy- 2-methylalkanoates 10j-m, with almost quantitative recovery of the enantiomerically pure 2-oxazolidinone 14.

Heterocyclic compounds and their production

A compound of the formula: STR1 wherein R1, R2, R3 and R4 are each a hydrogen atom, a lower alkyl group, an ar(lower)alkyl group or an aryl group, or R1 and R2 may be combined together to f