187332-12-3

Basic information

• Product Name: (S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE
• Synonyms: (S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE;(S)-(-)-4-(4-Hydroxybenzyl)-2-oxazolidine
• CAS NO: 187332-12-3
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.2
• Mol File: 187332-12-3.mol
• Article Data: 9

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE(187332-12-3)
• EPA Substance Registry System: (S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE(187332-12-3)

Safety Data

• Hazardous Substances Data: 187332-12-3(Hazardous Substances Data)

Usage

General Description

(S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE, also known as baclofen, is a medication used to treat muscle spasticity and spasm caused by conditions such as multiple sclerosis and spinal cord injuries. It works by acting on certain nerves in the brain and spinal cord to reduce muscle tightness and improve movement. Baclofen is a derivative of the neurotransmitter gamma-aminobutyric acid (GABA) and functions as a GABA receptor agonist, which means it activates these receptors in the central nervous system. This chemical is available in the form of oral tablets and intrathecal injections and should be used under the supervision of a healthcare professional. Common side effects may include drowsiness, dizziness, weakness, and nausea.

Upstream product

• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 40829-04-7 4-((S)-2-amino-3-hydroxy-propyl)-phenol hydrochloride 
• 66605-58-1 O-benzyl N-Boc-L-tyrosinol 
• 92515-43-0 (S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester 
• 3978-80-1 Boc-Tyr-OH 
• 60-18-4 L-tyrosine 
• 85803-44-7 (S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol 
• 16652-64-5 O-benzyl-S-tyrosine 
• 1080-06-4 L-Tyr-OMe 
• 215596-38-6 (S)-3-(4-hydroxyphenyl)-2-[(ethoxycarbonyl)amino]-1-propanoic acid methyl ester 
• 3417-91-2 L-tyrosine methyl ester HCl 
• 5034-68-4 4-[(2S)-2-amino-3-hydroxypropyl]phenol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 385842-97-7 (S)-2-amino-N-ethoxycarbonyl-3-(4-hydroxyphenyl)-propanol 

Downstream Products

• 170438-03-6 (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one 
• 191105-59-6 (S)-N-propionyl-4-(4-hydroxybenzyl)oxazolidin-2-one 
• 1010683-81-4 C₁₆H₁₉NO₄ 
• 63527-49-1 (R)-2-methylpent-4-enoic acid 
• 1010683-79-0 3-benzyl-4-(4S)-(4-hydroxybenzyl)oxazolidin-2-one 
• 1010683-80-3 (4S)-4-(4-hydroxybenzyl)-3-((2R)-2-methyl-3-phenylpropionyl)oxazolidin-2-one 
• 14367-67-0 2-methyl-3-phenylpropionic acid 
• 1010683-82-5 C₂₀H₂₁NO₄ 
• 1009-67-2 2-methyl-3-phenylpropionic acid 
• 1010683-83-6 C₁₇H₂₃NO₄ 
• 49642-51-5 (S)-(+)-2-methylhexanoic acid 
• 1010683-89-2 (R)-2-allylhexanoic acid 

Relevant articles and documents

Solid supported chiral auxiliaries in asymmetric synthesis. Part 2: Catalysis of 1,3-dipolar cycloadditions by Mg(II) cation

1,3-Dipolar cycloadditions of supported Evans' chiral auxiliary with nitrile oxides and nitrones in the presence of Mg(II) cation as catalyst were evaluated. The presence of acetonitrile as co-solvent was found to be fundamental for the Lewis acid catalysis on solid-phase. The regio- and stereochemical outcome of nitrile oxide cycloadditions is influenced by nearly stoichiometric quantities of the cation, whilst catalytic amounts of Mg(II) influence both the reactivity and the stereoselectivity of the nitrone cycloadditions. The results obtained support a reaction mechanism involving the coordination of the Mg(II) to the dicarbonyl fragment of the chiral auxiliary.

Sequencing of Sequence-Defined Oligourethanes via Controlled Self-Immolation

Sequence-defined polymers show promise for biomimetics, self-assembly, catalysis, and information storage, wherein the primary structure begets complex chemical processes. Here we report the solution-phase and the high-yielding solid-phase syntheses of discrete oligourethanes and methods for their self-immolative sequencing, resulting in rapid and robust characterization of this class of oligomers and polymers, without the use of MS/MS. Crucial to the sequencing is the inherent reactivity of the terminal alcohol to "unzip" the oligomers, in a controlled and iterative fashion, releasing each monomer as a 2-oxazolidinone. By monitoring the self-immolation reaction via LC/MS, an applied algorithm rapidly produces the sequence of the oligourethane. Not only does this process provide characterization of structurally complex molecules, it works as a reader of molecular information.

Asymmetric solution-phase mixture aldol reaction using oligomeric ethylene glycol tagged chiral oxazolidinones

Sorting tags are oligomeric structures that can be used as protecting groups or chiral auxiliaries enabling solution-phase mixture syntheses of multiple tagged compounds in one pot and allowing for facile and predictable chromatographic separation of products at the end of synthetic sequences. Perfluorinated hydrocarbon and oligomeric ethylene glycol (OEG) derivatives are known classes of sorting tags. Herein we describe the preparation of OEGylated chiral oxazolidinones and their use in asymmetric solution-phase mixture aldol reactions. Through the use of such oxazolidinones based on tyrosine four different individually tagged aldol adducts were obtained as a mixture, chromatographically demixed, detagged, and it was shown that these processes gave the desired aldol products in good yield and enantioselectivity.