132974-83-5

Basic information

• Product Name: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE
• Synonyms: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE;L-O-TBDPS-PYROGLUTAMINOL;(5S)-5-[[[(1,1-diMethylethyl)diphenylsilyl]oxy]Methyl]-2-Pyrrolidinone;(5S)-5-[[(tert-butyldiphenylsilyl)oxy]methyl]pyrrolidin-2-one;(5S)-5-[[[(tert-Butyl)diphenylsilyl]oxy]methyl]-2- pyrrolidinone;(5S)-5-[[[(tert-Butyl)diphenylsilyl]oxy]methyl]-2-pyrrolidinone,99%e.e.
• CAS NO: 132974-83-5
• Molecular Formula: C₂₁H₂₇NO₂Si
• Molecular Weight: 353.535
• Mol File: 132974-83-5.mol

Chemical Properties

• Melting Point: 81-83 °C(Solv: hexane (110-54-3))
• Boiling Point: 467.1±27.0 °C(Predicted)
• Appearance: /
• Density: 1.08±0.1 g/cm3(Predicted)
• PKA: 15.79±0.40(Predicted)
• CAS DataBase Reference: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE(132974-83-5)
• EPA Substance Registry System: (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE(132974-83-5)

Safety Data

• Hazardous Substances Data: 132974-83-5(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research:
(2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE is used as a potential candidate for drug development due to its unique chemical structure and chiral configuration. Its properties may be harnessed to create new therapeutic agents or improve existing ones.
Used in Organic Synthesis:
As a pyrrolidine derivative with a silicon-containing group, (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE can be utilized as an intermediate or building block in the synthesis of various organic compounds, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in Materials Science:
(2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE's unique structure and properties may also make it suitable for applications in materials science, such as the development of new polymers, coatings, or other advanced materials with specific characteristics.
Note: The specific applications and industries mentioned above are speculative, as the provided materials do not explicitly list any uses for (2S)-2-[[[(1,1-DIMETHYLETHYL)DIPHENYLSILYL]OXY]METHYL]-5-OXO-1-PYRROLIDINE. Further research and development would be required to confirm its potential uses in these areas.

Upstream product

• 58479-61-1 tert-butylchlorodiphenylsilane 
• 17342-08-4 (S)-Pyroglutaminol 
• 7149-65-7 ethyl (S)-pyroglutamate 
• 74936-93-9 (S)-5-oxopyrrolidine-2-carbonyl chloride 
• 98-79-3 L-Pyroglutamic acid 
• 4931-66-2 methyl (S)-pyroglutamate 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 

Downstream Products

• 138871-53-1 (S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-1-phenylselanyl-pyrrolidin-2-one 
• 138871-54-2 (S)-5-(tert-butyldiphenylsilyloxymethyl)-1-(phenylmethyl)-2-pyrrolidinone 
• 138629-30-8 (S)-tert-butyl 2-((tert-butyldiphenylsilyloxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 170148-26-2 (S)-2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-methoxy-3,4-dihydro-2H-pyrrole 
• 245648-28-6 (S)-benzyl 2-(((tert-butyldiphenylsilyl)oxy)methyl)-5-oxopyrrolidine-1-carboxylate 
• 144564-14-7 (4R,5S)-1-tert-butyloxycarbonyl-5-((tert-butyldiphenylsilyl)oxymethyl)-4-vinylpyrrolidin-2-one 
• 919349-69-2 (S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2-oxo-3-phenylselanyl-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 132974-88-0 (2S,3R,4S)-5-(tert-Butyl-diphenyl-silanyloxy)-3-ethyl-2-hydroxy-4-(toluene-4-sulfonylamino)-pentanoic acid 
• 132974-87-9 (3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-3-hydroxy-1-(toluene-4-sulfonyl)-pyrrolidin-2-one 
• 132974-92-6 (2S,3S,4R,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidine-2,3-diol 
• 132992-81-5 C₃₀H₃₇NO₅SSi 
• 132974-86-8 (4S,5S)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-4-ethyl-1-(toluene-4-sulfonyl)-pyrrolidin-2-one 
• 132975-04-3 (2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2-ethyl-3-(toluene-4-sulfonylamino)-butyric acid 
• 132974-90-4 (3R,4S)-4-(tert-Butyl-diphenyl-silanyloxymethyl)-3-ethyl-1-(toluene-4-sulfonyl)-azetidin-2-one 

Relevant articles and documents

Discovery and Development of 3-(6-Chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane Hydrochloride (SUVN-911): A Novel, Potent, Selective, and Orally Active Neuronal Nicotinic Acetylcholine α4β2 Receptor Antagonist for the Treatment of Depression

A series of chemical optimizations guided by in vitro affinity at the α4β2 receptor in combination with selectivity against the α3β4 receptor, pharmacokinetic evaluation, and in vivo efficacy in a forced swim test resulted in identification of 3-(6-chloropyridine-3-yloxymethyl)-2-azabicyclo[3.1.0]hexane hydrochloride (9h, SUVN-911) as a clinical candidate. Compound 9h is a potent α4β2 receptor ligand with a Ki value of 1.5 nM. It showed >10 μM binding affinity toward the ganglionic α3β4 receptor apart from showing selectivity over 70 other targets. It is orally bioavailable and showed good brain penetration in rats. Marked antidepressant activity and dose-dependent receptor occupancy in rats support its potential therapeutic utility in the treatment of depression. It does not affect the locomotor activity at doses several folds higher than its efficacy dose. It is devoid of cardiovascular and gastrointestinal side effects. Successful long-term safety studies in animals and phase-1 evaluation in healthy humans for safety, tolerability, and pharmacokinetics paved the way for its further development.

Approach to Fully Substituted Cyclic Nitrones from N-Hydroxylactam Derivatives: Development and Application to the Total Synthesis of Cylindricine C

An approach to cyclic nitrones from N-hydroxylactam derivatives is documented. The nucleophilic addition of an organolithium reagent to an N-OSEM [SEM=2-(trimethylsilyl)ethoxymethyl] lactam forms a five-membered chelated intermediate, which undergoes both elimination and deprotection to give a fully substituted nitrone in a one-pot process. When combined with the N-oxidation of easily available chiral lactams, this method becomes especially useful for the quick synthesis of chiral nitrones in enantio-pure form, enabling the concise total synthesis of cylindricine C.

Practical Synthesis of Chiral N-Heterocyclic Carbene Triazolium Salts Containing a Hydroxy Functional Handle

A library of functionalized chiral pyrrolidine-based N-heterocyclic carbene triazolium salts containing a hydroxy handle is prepared from readily accessible chiral (S)-pyroglutamic acid in eight steps. This improved synthetic protocol affords increased yields for known structures and 18 new NHCs are prepared by this method. The presence of a hydroxy handle offers potential for further functionalization and for non-covalent control over catalytic reactions in which the NHCs can serve as organocatalysts or ligands for organometallic catalysis.

A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds

Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.

BACTERIAL EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula I and salts thereof. Also disclosed are compositions comprising compounds of formula I and methods using compounds of formula I.

INDOLE DERIVATIVES AS EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula (I): and salts thereof. Also disclosed are compositions comprising compounds of formula I and compounds of formula I for use in treating or preventing bacterial infections.

BACTERIAL EFFLUX PUMP INHIBITORS

Disclosed herein are compounds of formula I: and salts thereof. Also disclosed are compositions comprising compounds of formula I and methods using compounds of formula I.

3-ARYL AND HETEROARYL SUBSTITUTED 5-TRIFLUOROMETHYL OXADIAZOLES AS HISTONE DEACETYLASE 6 (HDAC6) INHIBITORS

The present invention is directed to substituted 5-trifluoromethyl oxadiazole compounds of generic formula (I) or a pharmaceutically acceptable salt thereof. In particular, the invention is directed to a class of aryl and heteroaryl substituted 5-trifluoromethyl oxadiazole compounds of formula I which may be useful as HDAC6 inhibitors for treating cellular proliferative diseases, including cancer, neurodegenerative diseases, such as schizophrenia and stroke, as well as other diseases.

SUBSTITUTED HETEROCYCLIC SULFONAMIDE COMPOUNDS USEFUL AS TRPA1 MODULATORS

The invention is concerned with the compounds of formula I or II: and salts thereof. In addition, the present invention relates to methods of manufacturing and methods of using the compounds of formula I or II as well as pharmaceutical compositions containing such compounds. The compounds may be useful in treating diseases and conditions mediated by TRPA1, such as pain.

Methanesulfonic acid mediated cyclization and meyer-schuster rearrangement of γ-amino-ynones: Access to enantiopure pyrrolidine exocyclic vinylogous amides

α- and β-Amino-ynones have been largely used to prepare heterocyclic rings in the presence of various electrophiles such as protic acids or gold(I). Herein we disclose the unprecedented formation of pyrrolidine exocyclic vinylogous amides, in place of the expected azepinones or piperidinones, starting from γ-amino-ynones derived from amino acids. The process involves a tandem 1,2-addition of the protected nitrogen to the carbonyl group followed by a Meyer-Schuster rearrangement, which efficiently afforded enantiopure pyrrolidine exocyclic vinylogous amides. The sequence is poorly catalyzed by gold salts, but proved to be very efficient in the presence of methanesulfonic acid. Copyright