63853-74-7

Usage

Uses

Used in Pharmaceutical Industry:
5-METHOXY-2-PYRROLIDINONE is used as a synthetic intermediate for the production of various pharmaceutical compounds. Its unique structure allows it to be easily modified and incorporated into complex molecules, making it a valuable tool for the development of new drugs.
Used in the Synthesis of γ-Lactam Antibiotics:
5-METHOXY-2-PYRROLIDINONE is used as a key intermediate in the synthesis of γ-lactam analogs of penems and carbapenems. These antibiotics are known for their broad-spectrum activity against a wide range of bacteria, including antibiotic-resistant strains. The incorporation of 5-METHOXY-2-PYRROLIDINONE into these compounds enhances their stability and effectiveness, leading to improved treatment outcomes for patients.
Used in Organic Synthesis:
5-METHOXY-2-PYRROLIDINONE is used as a versatile intermediate in organic synthesis for the preparation of various organic compounds. Its reactivity allows it to participate in a range of chemical reactions, such as nucleophilic addition, substitution, and rearrangement reactions. This makes it a valuable building block for the synthesis of complex organic molecules, including pharmaceuticals, agrochemicals, and specialty chemicals.
Used in the Production of Fine Chemicals:
5-METHOXY-2-PYRROLIDINONE is used as an intermediate in the production of fine chemicals, which are high-purity chemicals used in various applications, such as research, diagnostics, and the synthesis of other specialty chemicals. Its unique properties and reactivity make it an essential component in the synthesis of these high-value products.

InChI:InChI=1/C5H9NO2/c1-8-5-3-2-4(7)6-5/h5H,2-3H2,1H3,(H,6,7)

Upstream product

• 616-45-5 2-pyrrolidinon 
• 67-56-1 methanol 
• 123-56-8 Succinimide 
• 33744-04-6 1-chloropyrrolidin-2-one 
• 62312-55-4 rac-4-hydroxy-2-pyrrolidone 
• 39662-63-0 5-ethoxy-pyrrolidin-2-one 
• 149-87-1 Pyroglutamic acid 
• 124-41-4 sodium methylate 

Downstream Products

• 41194-03-0 1-benzyl-5-methoxypyrrolidin-2-one 
• 128628-08-0 3-Oxo-2-(5-oxo-pyrrolidin-2-yl)-3-phenyl-propionic acid ethyl ester 
• 119984-22-4 1-benzoyl 5-methoxy pyrrolidin-2-one 
• 128628-10-4 5,5-Dimethyl-2-(5-oxo-pyrrolidin-2-yl)-cyclohexane-1,3-dione 
• 82259-09-4 (racemic)-5-(2'-propenyl)-2-pyrrolidinone 
• 879-37-8 3-indolylacetamide 
• 89017-55-0 5-(1,2-propadien-1-yl)-2-pyrrolidone 
• 1180503-93-8 C₁₅H₁₇NO₂ 
• 7529-16-0 5(S)-Vinyl-2-Pyrrolidinone 
• 76284-14-5 5-(phenylamino)pyrrolidin-2-one 
• 76284-15-6 5-(benzylamino)pyrrolidin-2-one 
• 91703-06-9 5-(4-phenylpiperazin-1-yl)pyrrolidin-2-one 

Relevant academic research and scientific papers

Cesium salts as superior catalysts for solvent-free modifications of biosourced pterolactam

γ-Lactam derivatives are widespread biologically active compounds, covering a large range of activities. Following our interest in both medicinal and green chemistries, we developed an original, cesium salts-mediated, scalable and solvent-free methodology to transform biosourced pyroglutamic acid and its derivatives to their N,N′-aminals, N,O,N,S-acetals and C5-substituted γ-lactams in good to excellent yields. This protocol is applicable to a large range of substrates, conducting to C5-substituted γ-lactam derivatives as potential new biologically active compounds.

Catalyst-free Mannich-type reaction of 1-(N-acylamino)alkyltriphenylphosphonium salts with silyl enolates

A catalyst-free reaction of 1-(N-acylamino)alkyltriphenylphosphonium tetrafluoroborates with silyl enolates was developed to prepare β-amino carbonyl compounds. The reported method is a useful approach for the preparation of N-protected β-amino esters as

3,5-Disubstituted-indole-7-carboxamides as IKKβ Inhibitors: Optimization of Oral Activity via the C3 Substituent

IκB kinase β (IKKβ or IKK2) is a key regulator of nuclear factor kappa B (NF-κB) and has received attention as a therapeutic target. Herein we report on the optimization of a series of 3,5-disubstituted-indole-7-carboxamides for oral activity. In doing so

Intramolecular [4+2] cycloaddition in n-allyl- and n-propargyl-α-furyl lactams

The size of nitrogen heterocycle in N-allyl- and N-propargyl-α-furyl lactams, as well as the nature of the unsaturated substituent linked to the nitrogen atom affected the possibility of thermal intramolecular [4+2] cycloaddition between multiple bond and the furan ring. N-Allyl-γ-(α-furyl)butyrolactam was shown to be unreactive at temperatures from 140 to 230°С. Substituted δ-valero- and ε-caprolactams underwent partial Diels–Alder cyclization, forming tautomeric mixtures that contained both the initial open-chain form and the cyclic form (diastereomeric 3a,6-epoxyisoindoles fused with an aza ring) in ratios between 19:81 and 55:45. N-Propargyl-α-furyl lactams did not participate in thermal IMDAF reaction regardless of the ring size and the temperature of the synthesis.

Impact of Functional Groups on the Copper-Initiated N-Arylation of 5-Functionalized Pyrrolidin-2-ones and Their Vinylogues

The electronic effects governing the N-arylation of pyrrolidone were investigated. The generalization of our preliminary findings on a copper(I)-catalyzed Csp2-N coupling process was first improved with a wide variety of aryl and heteroaryl halides and methyl pyroglutamate. The optimized protocol was further extended to pyrrolidin-2-ones substituted at the C5-position with an aryl group bearing an electron-donating or electron-withdrawing group as well as to some of their substituted enaminoester vinylogues. The impact of substituents at the N- and C5-position on these coupling processes seemed to be pivotal for determining both the reaction profiles and yields.

N-[1-(Benzotriazol-1-yl)alkyl]amides from N-acyl-α-amino acids or N-alkylamides

A variety of N-(1-methoxyalkyl)amides react with benzotriazole in the presence of PPh3·HBF4 and organic bases (Hünig's base, DBU or DABCO) or solid-state-supported bases (SiO2-Pip or IRA-67) in CHCl3 to give N-[

1-(N -acylamino)alkyl sulfones from N -acyl-α-amino acids or N -alkylamides

A variety of N-(1-methoxyalkyl)amides or carbamates react readily with sodium aryl sulfinates in the presence of triphenylphosphonium tetrafluoroborate or bromide in CHCl3 under mild conditions to give 1-(N-acylamino)alkyl sulfones in good yiel

Process for preparing 4-amino-5-hexenoic acid from succinimide

The present invention relates to a competitive process for the preparation of 4-amino-5-hexenoic acid and intermediates thereof. This compound is a well-known anti-epileptic drug for which several syntheses have been developed, all of them presenting drawbacks. The preparation process according to the present invention is very competitive from an economical point of view and is adapted to industrial scale preparation of 4-amino-5-hexenoic acid.

Expedient pyrrolizidine synthesis by propargylsilane addition to N-acyliminium ions followed by gold-catalyzed α-allenyl amide cyclization

(Chemical Equation Presented) A reaction sequence, involving the addition of (substituted) propargylsilanes to lactam-derived N-acyliminium ions followed by gold-catalyzed cyclization of the resulting α-allenyl amide, is applied in expedient syntheses of

Development of an electrolytic system for non-kolbe electrolysis based on the acid-base reaction between carboxylic acids as a substrate and solid-supported bases

We have successfully developed a novel electrolytic system for non-Kolbe electrolysis based on the acid-base reaction between carboxylic acids as a substrate and solid-supported bases. It was found that the acid-base reaction between carboxylic acids and solid-supported basespreferentially takes place to reduce the cell voltage in MeOH. On the basis of the electrolytic system, non-Kolbe electrolysis of various carboxylic acids was carried out to provide the corresponding methoxylated products in excellent yields. Copyright