145589-03-3

Basic information

• Product Name: (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one
• Synonyms: (R)-3-(3-methylbutanoyl)-4-benzyloxazolidin-2-one;Oxazolidinone, 3-(3-methyl-1-oxobutyl)-4-(phenylmethyl)-, (4R)-;3-isovaleroyl-4(R)-benzyl-oxazolidin-2-one;(4R)-4-benzyl-3-(3-Methylbutanoyl)-1,3-oxazolidin-2-one;3-(3-Methyl-1-oxobutyl)-4-(p henylMethyl)-, (R)-2-Oxazolidinone;(4R)-3-(3-Methyl-1-oxobutyl)-4-(phenylMethyl)-2-oxazolidinone;(4R)-4-Benzyl-3-isovaleryloxazolidin-2-one;4R-Benzyl-3-(3-Methylbutyryl)oxazolidin-2-one
• CAS NO: 145589-03-3
• Molecular Formula: C₁₅H₁₉NO₃
• Molecular Weight: 261.31626
• Product Categories: Aromatics;Chiral Reagents;Miscellaneous Reagents
• Mol File: 145589-03-3.mol

Chemical Properties

• Boiling Point: 412.912 °C at 760 mmHg
• Flash Point: 203.522 °C
• Appearance: White solid
• Density: 1.152
• Vapor Pressure: 5E-07mmHg at 25°C
• Refractive Index: 1.541
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility: Chloroform, Dichloromethane, Ethyl Acetate
• PKA: -2.33±0.40(Predicted)
• CAS DataBase Reference: (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one(145589-03-3)
• EPA Substance Registry System: (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one(145589-03-3)

Safety Data

• Safety Statements: 24/25
• Hazardous Substances Data: 145589-03-3(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one is used as an intermediate in the synthesis of pharmaceutical compounds for [application reason]. Its specific role in the synthesis process allows for the development of new drugs with potential therapeutic benefits.
Used in Chemical Research:
In the field of chemical research, (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one is used as a research compound for [application reason]. Its unique properties and reactivity contribute to the advancement of scientific knowledge and the discovery of new chemical reactions and processes.
Used in Material Science:
(R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one is also utilized in material science as a component in the development of new materials with specific properties for [application reason]. Its incorporation into these materials can lead to improved performance and novel applications in various industries.
Used in Agrochemical Industry:
In the agrochemical industry, (R)-3-(3-Methylbutanoyl)-4-benzyloxazolidin-2-one is used as a building block for the creation of new agrochemicals for [application reason]. Its role in the synthesis of these compounds can contribute to the development of more effective and environmentally friendly products for agricultural use.

InChI:InChI=1/C15H19NO3/c1-11(2)8-14(17)16-13(10-19-15(16)18)9-12-6-4-3-5-7-12/h3-7,11,13H,8-10H2,1-2H3/t13-/m1/s1

Upstream product

• 503-74-2 3-methylbutyric acid 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 
• 108-12-3 isopentanoyl chloride 
• 40217-17-2 (R)-4-(phenylmethyl)-2-oxazolidinone 
• 5292-43-3 bromoacetic acid tert-butyl ester 
• 63-91-2 L-phenylalanine 
• 134807-37-7 (4S)-3-((2S)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 100-51-6 benzyl alcohol 
• 90719-30-5 (4S)-3-((E)-2-butenoyl)-4-benzyl-2-oxazolidinone 
• 1184-58-3 dimethylaluminum chloride 

Downstream Products

• 104266-96-8 (3(2S),4S)-3-(2-(N,N'-bis-(t-butoxycarbonyl)hydrazino)-3-methyl-1-oxobutyl)-4-(phenylmethyl)-2-oxazolidinone 
• 128948-72-1 (4S)-4-benzyl-3-<(2S,4E)-6-cyclohexyl-2-isopropylhex-4-enoyl>oxazolidin-2-one 
• 113543-35-4 (4S)-3-(2-bromo-3-methyl-1-oxobutyl)-4-(phenylmethyl)-2-oxazolidinone 
• 136546-81-1 (S)-4-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-5-methyl-hexanenitrile 
• 156546-62-2 (S)-4-Benzyl-3-((S)-3-methyl-2-phenylsulfanyl-butyryl)-oxazolidin-2-one 
• 191664-12-7 N-[(R)-2-((S)-4-Benzyl-2-oxo-oxazolidine-3-carbonyl)-3-methyl-butyl]-benzamide 
• 172900-80-0 2(R)-isopropyl-3-(p-tert-butyl-phenyl)-propanol 
• 240821-65-2 (4S)-3-[(2S)-2-(1-methylethyl)-1-oxopent-4-en-1-yl]-4-(phenylmethyl)oxazolidin-2-one 
• 134807-37-7 (4S)-3-((2S)-4-(tert-butoxy)-2-(1-methylethyl)-4-oxobutanoyl)-4-(phenylmethyl)-1,3-oxazolidin-2-one 
• 117037-09-9 (S)-4-Benzyl-3-((S)-2-benzyl-3-methyl-butyryl)-oxazolidin-2-one 
• 470454-06-9 4-(R)-benzyl-3-(2-(R)-benzyloxymethyl-3-methylbutyryl)oxazolidin-2-one 
• 656241-29-1 (S)-4-Benzyl-3-{(S)-2-[4-methoxy-3-(3-methoxy-propoxy)-benzyl]-3-methyl-butyryl}-oxazolidin-2-one 
• 669074-37-7 (S)-4-Benzyl-3-((S)-2-fluoro-3-methyl-butyryl)-oxazolidin-2-one 
• 117037-20-4 (S)-2-Benzyl-3-methyl-butyric acid 

Relevant articles and documents

An improved and economical process for the manufacture of the key intermediate of aliskiren, a new potent renin inhibitor

An improved, practical, economical and efficient process for the production of (2S,4S)-2-amino-4-(4-methoxy-3-(3-methoxypropoxy)benzyl)-5-methylhexanoic acid, a key intermediate of the new potent renin inhibitor of aliskiren, in a total yield over 30% is described. This process avoids expensive reagents and chromatographic purifications, and is easily scaled up in industry.

Structure-based drug design of novel and highly potent pyruvate dehydrogenase kinase inhibitors

Pyruvate dehydrogenase kinases (PDHKs) are fascinating drug targets for numerous diseases, including diabetes and cancers. In this report, we describe the result of our structure-based drug design from tricyclic lead compounds that led to the discovery of highly potent PDHK2 and PDHK4 dual inhibitors in enzymatic assay. The C3-position of the tricyclic core was explored, and the PDHK2 X-ray structure with a representative compound revealed a novel ATP lid conformation in which the phenyl ring of Phe326 mediated the interaction of the Arg258 sidechain and the compound. Compounds with amide linkers were designed to release the ATP lid by forming an intramolecular pi-pi interaction, and these compounds showed single-digit nM IC50 values in an enzymatic assay. We also explored the C4-position of the tricyclic core to reproduce the interaction observed with the C3-position substitution, and the pyrrolidine compound showed the same level of IC50 values. By optimizing an interaction with the Asn255 sidechain through a docking simulation, compounds with 2-carboxy pyrrole moiety also showed single-digit nM IC50 values without having a cation-pi interaction with the Arg258 sidechain.

JAK INHIBITORS

Described herein are Janus kinase (JAK) inhibitors and methods of utilizing JAK inhibitors in the treatment of diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.

JAK INHIBITORS

Described herein are Janus kinase (JAK) inhibitors and methods of utilizing JAK inhibitors in the treatment of diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.

JAK INHIBITORS

Described herein are Janus kinase (JAK) inhibitors and methods of utilizing JAK inhibitors in the treatment of diseases, disorders or conditions. Also described herein are pharmaceutical compositions containing such compounds.

A Highly Selective Hydantoin Inhibitor of Aggrecanase-1 and Aggrecanase-2 with a Low Projected Human Dose

Aggrecanase-1 and -2 (ADAMTS-4 and ADAMTS-5) are zinc metalloproteases involved in the degradation of aggrecan in cartilage. Inhibitors could provide a means of altering the progression of osteoarthritis. We report the identification of 7 which had good oral pharmacokinetics in rats and showed efficacy in a rat chemical model of osteoarthritis. The projected human dose required to achieve sustained plasma levels ≥10 times the hADAMTS-5 IC50 is 5 mg q.d.

A preparation N-substituted oxazole alkone chiral method of ligand

The invention relates to the technical field of a method for preparing an N-substituted oxazolone chiral ligand. The method for preparing the N-substituted oxazolone chiral ligand provided by the invention comprises the following steps of: reacting a compound A shown as the following formula (described in the specification) with R1-COC1 under the action of alkaline reagent potassium tert-butoxide, sodium methyoxide or NaNH2 to obtain a target product (I), wherein R1 is an alkyl with the number of carbon atoms of being less than or equal to 7, and R2 is phenyl, benzyl or isopropyl. In the invention, potassium tert-butoxide is used for substituting butyl lithium and lithium bis(trimethylsilyl)amide which are frequently used in the prior art, reaction can be carried out at normal temperature, reaction time is shortened, reaction is completed after batch charging is completed, then aftertreatment operation can be carried out, and dynamic cost is saved; less gas is released in the aftertreatment process, and safety is high; and yield of the obtained target compound is high, and purity is high, thus the method provided by the invention is applicable to industrial production.

Rational Design of Thermodynamic and Kinetic Binding Profiles by Optimizing Surface Water Networks Coating Protein-Bound Ligands

A previously studied congeneric series of thermolysin inhibitors addressing the solvent-accessible S2′ pocket with different hydrophobic substituents showed modulations of the surface water layers coating the protein-bound inhibitors. Increasing stabilization of water molecules resulted in an enthalpically more favorable binding signature, overall enhancing affinity. Based on this observation, we optimized the series by designing tailored P2′ substituents to improve and further stabilize the surface water network. MD simulations were applied to predict the putative water pattern around the bound ligands. Subsequently, the inhibitors were synthesized and characterized by high-resolution crystallography, microcalorimetry, and surface plasmon resonance. One of the designed inhibitors established the most pronounced water network of all inhibitors tested so far, composed of several fused water polygons, and showed 50-fold affinity enhancement with respect to the original methylated parent ligand. Notably, the inhibitor forming the most perfect water network also showed significantly prolonged residence time compared to the other tested inhibitors.

Convergent Synthesis of the Renin Inhibitor Aliskiren Based on C5-C6 Disconnection and CO2H-NH2 Equivalence

A novel synthesis of the renin inhibitor aliskiren based on an unprecedented disconnection between C5 and C6 was developed, in which the C5 carbon acts as a nucleophile and the amino group is introduced by a Curtius rearrangement, which follows a simultaneous stereocontrolled generation of the C4 and C5 stereogenic centers by an asymmetric hydrogenation. Operational simplicity, step economy, and a good overall yield makes this synthesis amenable to manufacture on scale.

A Facile, Six-Step Process for the Synthesis of (3 S,5 S)-3-Isopropyl-5-((2 S,4 S)-4-isopropyl-5-oxo-tetrahydrofuran-2-yl)-2-oxopyrrolidine-1-carboxylic Acid tert -Butyl Ester, the Key Synthetic Intermediate of Aliskiren

A facile, six-step process for the synthesis of (3S,5S)-3-isopropyl-5-((2S,4S)-4-isopropyl-5-oxotetrahydro- furan-2-yl)-2-oxopyrrolidine-1-carboxylic acid tert-butyl ester from (S)-4-benzyloxazolidin-2-one 2 in an overall 50% yield is reported. The key transformations include: a highly efficient diastereoselective epoxidation, Lewis acid-catalyzed ring-opening with bromide, an SN2 reaction using NaN3, and a tandem reduction-cyclization reaction.