Heterocyclic Building Blocks-Oxazolidine

On January 31, 2007, Gourlay, Matthew D.; Kendrick, John; Leusen, Frank J. J. published an article.Synthetic Route of 97859-49-9 The title of the article was Rationalization of racemate resolution: predicting spontaneous resolution through crystal structure prediction. And the article contained the following:

Crystal structure prediction simulations are reported on 5-hydroxymethyl-2-oxazolidinone and 4-hydroxymethyl-2-oxazolidinone to establish the feasibility of predicting the spontaneous resolution of racemates of small organic mols. It is assumed that spontaneous resolution occurs when the enantiomorph is more stable than the racemic solid. The starting point is a gas phase conformational search to locate all low-energy conformations. These conformations were used to predict the possible crystal structures of 5- and 4-hydroxymethyl-2-oxazolidinone. In both cases, the racemic crystal structure is predicted to have the lowest energy. The energy differences between the lowest-energy racemic solids and the lowest-energy enantiomorphs are 0.2 kcal mol-1 for 5-hydroxymethyl-2-oxazolidinone and 0.9 kcal mol-1 for 4-hydroxymethyl-2-oxazolidinone. In the case of 4-hydroxymethyl-2-oxazolidinone, where the racemic crystal is known to be more stable and the exptl. crystal structures of both the racemate and the enantiomorph are available, the simulation results match the observed data. For 5-hydroxymethyl-2-oxazolidinone, where only enantiopure crystals are observed exptl., the known exptl. structure is found 1.6 kcal mol-1 above the lowest-energy predicted structure. It is possible to predict whether the racemate of a small chiral mol. can be resolved spontaneously, although further advances in the accuracy of lattice energy calculations are required. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Synthetic Route of 97859-49-9

The Article related to spontaneous organic racemate resolution crystal structure prediction, Organic Analytical Chemistry: Separations and other aspects.Synthetic Route of 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On October 3, 2019, Qiu, Yao-Ling; Kass, Jorden; Suh, Byung-Chul; Cao, Hui; Li, Wei; Peng, Xiaowen; Gao, Xuri; Or, Yat Sun published a patent.Application In Synthesis of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the patent was Hepatitis B antiviral agents. And the patent contained the following:

The present invention discloses compounds of Formula (I; W and Y are each N and Z is CR10; or W is C, one of Y and Z is N and the other is NR11; R10 is hydrogen, halo, or optionally substituted C1-C6 alkyl; R11 is hydrogen, etc.), and pharmaceutically acceptable salts, esters, or prodrugs thereof which inhibit the protein(s) encoded by hepatitis B virus (HBV) or interfere with the function of the HBV life cycle of the hepatitis B virus and are also useful as antiviral agents. The present invention further relates to pharmaceutical compositions comprising the aforementioned compounds for administration to a subject suffering from HBV infection. The invention also relates to methods of treating an HBV infection in a subject by administering a pharmaceutical composition comprising the compounds of the present invention. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Application In Synthesis of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to hepatitis b virus antiviral, Pharmaceuticals: Formulation and Compounding and other aspects.Application In Synthesis of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On January 17, 2014, Mabe, Phillip J.; Zakarian, Armen published an article.Category: oxazolidine The title of the article was Asymmetric Radical Addition of TEMPO to Titanium Enolates. And the article contained the following:

A mild method for α-hydroxylation of N-acyl oxazolidinones by asym. radical addition of the 2,2,6,6-tetramethylpiperidine N-oxy (TEMPO) radical to titanium enolates was developed. The high diastereoselectivity and broad scope of the reaction show synthetic utility for the α-hydroxylation of substrates that are not tolerant to strongly basic conditions. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Category: oxazolidine

The Article related to asym radical addition tempo titanium enolate alpha hydroxylation, General Organic Chemistry: Synthetic Methods and other aspects.Category: oxazolidine

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On July 8, 2015, Jimenez, Jacqueline; Ramirez, JuanCarlos; Huelgas, Gabriela; Melendrez, Ruth; Cabrera-Vivas, Blanca M.; Sansinenea, Estibaliz; Ortiz, Aurelio published an article.Quality Control of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the article was ‘Syn-effect’ in the diastereoselective alkylation of 3-[(E)-α,β-unsaturated-γ-substituted]-N-acyloxazolidinones. And the article contained the following:

Synthetic methods for the formation of alkenes usually produce the E-alkene because it is more stable. However, in isomerization reaction (double bond migration) that takes place in α, β-unsaturated carbonyl compounds, when these carbonyl compounds are exposed to strong bases, furnish Z-alkenes highly stereoselective depending on the γ-substituent in the α, β-unsaturated carbonyl. This stereoselectivity can be attributed to the known Syn-effect. The synthetic value of this methodol. is the achievement of chiral alc. bearing an electron rich Z-alkene, as well as substituted, which was accomplished via removal of the oxazolidinone moiety under treatment with NaBH4, THF-H2O. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Quality Control of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to syn effect stereoselective alkylation unsaturated acyloxazolidinone, General Organic Chemistry: Synthetic Methods and other aspects.Quality Control of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On March 31, 1995, Davies, Stephen G.; Sanganee, Hitesh J. published an article.Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one The title of the article was 4-Substituted-5,5-dimethyl Oxazolidin-2-ones as effective chiral auxiliaries for enolate alkylations and Michael additions. And the article contained the following:

4-(Me, Ph, benzyl, and i-propyl)-5,5-dimethyloxazolidin-2-ones, readily available from α-amino acids, are shown to be effective chiral auxiliaries for stereoselective enolate alkylations and conjugate additions of attached N-acyl moieties. Thus, e.g., diastereoselective benzylation of the N-propionyl derivatives I (R = Me, Ph, benzyl, iso-Pr) afforded II (% yield/% d.e. in order of R: 85/90; 63/81; 51/95; 22/97). The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

The Article related to oxazolidinone dimethyl chiral auxiliary, chiral auxiliary dimethyloxazolidinone, stereoselective enolate alkylation michael addition dimethyloxazolidinone, General Organic Chemistry: Synthetic Methods and other aspects.Safety of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On March 5, 2021, Obrien, Kevin T.; Nadraws, Jonathan W.; Smith, Amos B. III published an article.Synthetic Route of 168297-86-7 The title of the article was A Difluoromethylene Linchpin/Synthon: Application in Conjunction with Anion Relay Chemistry (ARC) Permits Ready Access to Diverse Difluoromethylene Scaffolds. And the article contained the following:

Organodifluorine synthons, in conjuction with three-component diastereoselective anion relay chem. (ARC), permit ready access to diverse difluoromethylene scaffolds. Initiated via [1,2]-addition of an organolithium reagent to a β-difluoromethylene silyl aldehyde, an alkoxide intermediate is formed, which is capable of undergoing a [1,4]-Brook rearrangement to generate a stabilized α-difluoromethylene carbanion, which, upon electrophile capture, affords a three-component adduct. This three component synthetic tactic represents a novel one-pot divergent strategy for the construction of diverse organodifluorine containing compounds The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Synthetic Route of 168297-86-7

The Article related to aldehyde difluoromethylene silyl electrophile diastereoselective anion relay, difluoromethylene scaffold stereoselective preparation, Aliphatic Compounds: Halides and Halonium Compounds and other aspects.Synthetic Route of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On January 31, 2008, Wang, Guijun published an article.Application of 97859-49-9 The title of the article was Synthesis and antibacterial properties of oxazolidinones and oxazinanones. And the article contained the following:

A review. Oxazolidinones are important synthetic antibacterial agents useful for the treatment of multi-antibiotic resistant Gram-pos. bacterial infections. Since the launch of Linezolid, the first member of the oxazolidinone antibacterial family, there have been many studies directed towards structural optimization and the development of second generation oxazolidinones. The N-aryl 5-acetamido Me oxazolidinone is the core structure for this class of antibacterial agents and the oxazolidinone component is essential for antibacterial activities. The chiral cyclic carbamates, 5-hydroxymethyl-oxazolidin-2-one and 6-hydroxymethyl-[1,3]oxazinan-2-one, are also important building blocks for synthesizing other biol. active compounds Because of the importance of these compounds, many methods have been developed for their facile syntheses. In the first part of this paper, the synthesis of linezolid and its analogs, as well as the preparation of the oxazolidinone core structures, will be reviewed. Secondly, recent developments in the area of oxazolidinone antibacterial agents including structure-activity relationships (SAR) will be reviewed. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Application of 97859-49-9

The Article related to review oxazolidinone oxazinanone substituted preparation linezolid analog antibacterial agent, Heterocyclic Compounds (More Than One Hetero Atom): Reviews and other aspects.Application of 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On June 30, 2016, Shiers, Jason John; Watts, John Paul; Onions, Stuart Thomas; Abdul Quddus, Mohammed; Wrigglesworth, Joseph William; Sambrook-Smith, Colin Peter; Naylor, Alan; Londesbrough, Derek published a patent.Synthetic Route of 168297-86-7 The title of the patent was Preparation of pyridine, pyridazine and triazine derivatives for the treatment of cancer and/or other diseases. And the patent contained the following:

Title compounds I [one of Q1 and Q2 = N and the other = CH, or both Q1 and Q2 = N, and Q3 = CH; or Q1 , Q2 and Q3 = N; A = (un)substituted five- or six-membered aromatic ring; R1 = aliphatic carbocyclic or heterocyclic ring; R2 = H, alkyl or halo; R3 = aryl or heteroaryl; R5 and R6 independently = H or alkyl] and their pharmaceutically acceptable salts, are prepared and disclosed for the treatment of cancer. Thus, II was prepared in a multi-step synthesis starting from Et 2-(trans-4-aminocyclohexyl)acetate hydrochloride with CbzCl. Compounds of the invention were tested for their inhibitory activity in Akt activation assay, e.g., compound II showed IC50 value of 780 nM, 110 nM and 15 nM against Akt1 and Akt2 and Akt3. The experimental process involved the reaction of (S)-4-Isopropyl-5,5-dimethyloxazolidin-2-one(cas: 168297-86-7).Synthetic Route of 168297-86-7

The Article related to pyridine pyridazine triazine preparation cancer, Heterocyclic Compounds (More Than One Hetero Atom): Triazines and other aspects.Synthetic Route of 168297-86-7

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On June 24, 2016, Musicki, Branislav published a patent.SDS of cas: 97859-49-9 The title of the patent was Preparation of benzenesulfonamide derivatives as inverse agonists of retinoid-related orphan receptor gamma. And the patent contained the following:

The invention relates to the preparation of benzenesulfonamide derivatives I, wherein m is an integer 0-3; L is a bond, CH2; R1 is alkyl, cycloalkyl, alkenyl, alkyl-cycloalkyl, alkyl-heterocycloalkyl; R2 is H, halogen, alkyl, alkenyl, alkoxy, CN; R3 is H, alkyl, NH2; R4 is H, alkyl, alkoxy, ether, alkyl-amino-alkyl; A1 is substituted amine, O, S, SO, SO2, SO(=NH), CH2, C=C, alkylidene; A2 is bond, S, SO, SO2, sulfonimide, CH(OH), C(=O)O; Q1-Q5 are independently N, alkylidene, and the pharmaceutically acceptable addition salts thereof, the hydrates and/or solvates thereof, and the use of same as inverse agonists of retinoid-related orphan receptor gamma (RORγt). Thus, benzenesulfonamide II was prepared and tested in vitro as inverse agonist of retinoid-related orphan receptor gamma (IC50 = 100 nM – 1 μM). The invention is also relative to a composition pharmaceutical including such compounds like its use for the treatment by way topics and/or oral of the inflammatory diseases in particular the acne, the psoriasis and/or the atopic dermatitis. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).SDS of cas: 97859-49-9

The Article related to cosmetic atopic dermatitis psoriasis antiinflammatory receptor acne benzenesulfonamide preparation, human interleukin acne benzenesulfonamide preparation, Heterocyclic Compounds (More Than One Hetero Atom): Triazines and other aspects.SDS of cas: 97859-49-9

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem

On June 23, 2016, Musicki, Branislav published a patent.Safety of (R)-5-(Hydroxymethyl)oxazolidin-2-one The title of the patent was Preparation of benzenesulfonamide derivatives as inverse agonists of retinoid-related orphan receptor gamma. And the patent contained the following:

The invention relates to the preparation of benzenesulfonamide derivatives I, wherein q is an integer 0-3; L is a bond, CH2; R1 is alkyl, cycloalkyl, alkenyl, alkyl-cycloalkyl, alkyl-heterocycloalkyl; R2 is H, halogen, alkyl, alkenyl, alkoxy, CN; R3 is H, alkyl, NH2; R4 is H, alkyl, alkoxy, ether, alkyl-amino-alkyl; A1 is substituted amine, O, S, SO, SO2, SO(=NH), CH2, C=C, alkylidene; A2 is bond, S, SO, SO2, sulfonimide, CH(OH), C(=O)O; Q1-Q5 are independently N, alkylidene, and the pharmaceutically acceptable addition salts thereof, the hydrates and/or solvates thereof, and the use of same as inverse agonists of retinoid-related orphan receptor gamma (RORγt). Thus, benzenesulfonamide II was prepared and tested in vitro as inverse agonist of retinoid-related orphan receptor gamma (IC50 = 100 nM – 1 μM). The invention also relates to pharmaceutical compositions comprising such compounds, as well as to the use thereof for the topical and/or oral treatment of RORγt receptor-mediated inflammatory diseases, in particular acne, psoriasis and/or atopic dermatitis. The experimental process involved the reaction of (R)-5-(Hydroxymethyl)oxazolidin-2-one(cas: 97859-49-9).Safety of (R)-5-(Hydroxymethyl)oxazolidin-2-one

The Article related to human interleukin acne benzenesulfonamide preparation, cosmetic atopic dermatitis psoriasis antiinflammatory receptor acne benzenesulfonamide preparation, Heterocyclic Compounds (More Than One Hetero Atom): Triazines and other aspects.Safety of (R)-5-(Hydroxymethyl)oxazolidin-2-one

Referemce:
Oxazolidine – Wikipedia,
Oxazolidine | C3H7NO – PubChem