187332-12-3

Usage

Uses

Used in Pharmaceutical Industry:
(S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE is used as a muscle relaxant for the treatment of muscle spasticity and spasms caused by conditions such as multiple sclerosis and spinal cord injuries. It acts on specific nerves in the brain and spinal cord to reduce muscle tightness and improve movement.
Used in Neurological Treatments:
(S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE is used as a GABA receptor agonist in neurological treatments, targeting the central nervous system to alleviate muscle spasticity and spasms. Its agonist activity on GABA receptors contributes to its effectiveness in managing muscle-related conditions.
Used in Medical Supervision:
(S)-(-)-4-(4-HYDROXYBENZYL)-2-OXAZOLIDINONE is used under the supervision of healthcare professionals to ensure safe and effective administration. This is important due to its potential side effects, which may include drowsiness, dizziness, weakness, and nausea.

Upstream product

• 385842-97-7 (S)-2-amino-N-ethoxycarbonyl-3-(4-hydroxyphenyl)-propanol 
• 5034-68-4 4-[(2S)-2-amino-3-hydroxypropyl]phenol 
• 530-62-1 1,1'-carbonyldiimidazole 
• 1080-06-4 L-Tyr-OMe 
• 16652-64-5 O-benzyl-S-tyrosine 
• 60-18-4 L-tyrosine 
• 3978-80-1 Boc-Tyr-OH 
• 92515-43-0 (S)-3-(4-benzyloxyphenyl)-2-(tert-butoxycarbonylamino)propionic acid benzyl ester 
• 66605-58-1 O-benzyl N-Boc-L-tyrosinol 
• 332-25-2 4-(trifluoromethoxy)benzonitrile 
• 40829-04-7 4-((S)-2-amino-3-hydroxy-propyl)-phenol hydrochloride 
• 85803-44-7 (S)-2-amino-3-(4-benzyloxyphenyl)-1-propanol 
• 215596-38-6 (S)-3-(4-hydroxyphenyl)-2-[(ethoxycarbonyl)amino]-1-propanoic acid methyl ester 
• 170438-03-6 (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one 

Downstream Products

• 103-25-3 3-phenylpropanoic acid methyl ester 
• 501-52-0 3-Phenylpropionic acid 
• 170438-03-6 (S)-4-(4-(benzyloxy)benzyl)oxazolidin-2-one 
• 1010683-87-0 C₂₂H₂₅NO₄ 
• 117037-20-4 (S)-2-Benzyl-3-methyl-butyric acid 
• 1010683-88-1 C₁₈H₂₃NO₄ 
• 254890-16-9 (2S)-2-(1-Methylethyl)pent-4-enoic acid 
• 1010683-86-9 C₁₆H₂₁NO₄ 
• 15071-34-8 (2S)-2,3-Dimethylbutanoic acid 
• 1010683-84-7 C₂₃H₂₇NO₄ 
• 5668-19-9 (2R)-2-Benzylhexanoic acid 
• 1010683-89-2 (R)-2-allylhexanoic acid 
• 1010683-85-8 C₁₉H₂₅NO₄ 
• 1010683-83-6 C₁₇H₂₃NO₄ 

Relevant academic research and scientific papers

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.

Solution- and solid-phase synthesis of enantiomerically pure spiro oxindoles

A convenient synthesis of enantiomerically pure oxindoles using a three component reaction involving 1:3 dipolar cycloaddition reaction has been achieved using solution and solid phase chemistry.

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.

Visible-Light-Mediated Liberation and In Situ Conversion of Fluorophosgene

The first example for the photocatalytic generation of a highly electrophilic intermediate that is not based on radical reactivity is reported. The single-electron reduction of bench-stable and commercially available 4-(trifluoromethoxy)benzonitrile by an organic photosensitizer leads to its fragmentation into fluorophosgene and benzonitrile. The in situ generated fluorophosgene was used for the preparation of carbonates, carbamates, and urea derivatives in moderate to excellent yields via an intramolecular cyclization reaction. Transient spectroscopic investigations suggest the formation of a catalyst charge-transfer complex-dimer as the catalytic active species. Fluorophosgene as a highly reactive intermediate, was indirectly detected via its next downstream carbonyl fluoride intermediate by NMR. Furthermore, detailed NMR analyses provided a comprehensive reaction mechanism including a water dependent off-cycle equilibrium.

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.

A practical synthesis of enantiopure (S)-4-(4-hydroxybenzyl)-oxazolidin-2-one

A high yielding four-step synthesis of enantiopure 4-(4-hydroxybenzyl)-oxazolidin-2-one (S)-1 from N-Boc-L-tyrosine is described. (S)-1 is a key intermediate for the preparation of a number of polymer supported Evans' oxazolidin-2-ones that have been employed previously for solid supported asymmetric synthesis.

(4S)-p-hydroxybenzyl-1,3-oxazolidin-2-one as a solid-supported chiral auxiliary in asymmetric 1,3-dipolar cycloadditions

Evans' chiral auxiliary was grafted onto both Merrifield and Wang resins and, after functionalisation, they were used as chiral dipolarophiles in a 1,3-dipolar cycloaddition involving both a nitrile oxide and a nitrone. The cycloadducts were cleaved and analysed by chiral HPLC: the recovered supported chiral oxazolidinone was functionalised and reused in further cycloadditions. The stereochemical results as well as the possibility of recycling the chiral linker supports the applicability of solid-supported chiral auxiliaries. (C) 2000 Elsevier Science Ltd.

Synthesis of chiral α-substituted β-hydroxy acid derivatives on solid support

Enantioselective aldol condensation using solid supported chiral auxiliary was used for the synthesis of α-substituted-β-hydroxy acid and ester. The solid phase synthesis proceeded with high degree of enatioselectivity, as is observed in solution chemistry.

An Improved Preparation of Oxazolidin-2-one Chiral Auxiliaries

Reduction of carbamate-blocked amino esters by lithium borohydride (made in situ from sodium borohydride and lithium iodide) forms chiral 4-substituted oxazolidin-2-ones directly. The presence of iodide in the reaction mixture appears to promote the cyclization of the intermediate alkoxyborohydride. This provides a route to these important chiral auxiliaries, employing less hazardous reagents and simpler reaction conditions than do most existing methods.