103539-32-8

Basic information

• Product Name: METHYL (R)-AZIRIDINE-2-CARBOXYLATE
• Synonyms: 2-Aziridinecarboxylic acid, methyl ester, (R)- (9CI)
• CAS NO: 103539-32-8
• Molecular Formula: C₄H₇NO₂
• Molecular Weight: 101.1
• Mol File: 103539-32-8.mol

Chemical Properties

• Boiling Point: 117.9°Cat760mmHg
• Flash Point: 25.1°C
• Appearance: /
• Density: 1.163g/cm³
• Vapor Pressure: 17.1mmHg at 25°C
• Refractive Index: 1.453
• PKA: 5.76±0.40(Predicted)
• CAS DataBase Reference: METHYL (R)-AZIRIDINE-2-CARBOXYLATE(CAS DataBase Reference)
• NIST Chemistry Reference: METHYL (R)-AZIRIDINE-2-CARBOXYLATE(103539-32-8)
• EPA Substance Registry System: METHYL (R)-AZIRIDINE-2-CARBOXYLATE(103539-32-8)

Safety Data

• Hazardous Substances Data: 103539-32-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
METHYL (R)-AZIRIDINE-2-CARBOXYLATE is used as a key intermediate or building block in the synthesis of various pharmaceuticals. Its unique structure allows for the creation of complex molecules with potential therapeutic applications, making it an essential component in the development of new drugs.
Used in Agrochemical Industry:
In the agrochemical sector, METHYL (R)-AZIRIDINE-2-CARBOXYLATE serves as a crucial intermediate in the production of pesticides and other crop protection agents. Its reactivity and chiral nature enable the synthesis of highly effective and selective compounds, contributing to improved agricultural practices and crop yields.
Used in Fine Chemicals Industry:
METHYL (R)-AZIRIDINE-2-CARBOXYLATE is utilized as a versatile building block in the synthesis of fine chemicals, including specialty chemicals and advanced materials. Its unique properties facilitate the development of innovative products with diverse applications, such as in the fields of fragrances, dyes, and coatings.
Used in Medicinal Chemistry Research:
METHYL (R)-AZIRIDINE-2-CARBOXYLATE is employed as a valuable tool in medicinal chemistry research, where its potential applications are explored for the development of novel therapeutic agents. Its unique structure and reactivity make it an attractive candidate for the design and synthesis of bioactive molecules with potential use in treating various diseases and conditions.
Used in Material Science:
In the field of material science, METHYL (R)-AZIRIDINE-2-CARBOXYLATE is used for the development of new materials with specific properties. Its unique structure and reactivity contribute to the creation of advanced materials with potential applications in various industries, such as electronics, aerospace, and nanotechnology.

InChI:InChI=1/C4H7NO2/c1-7-4(6)3-2-5-3/h3,5H,2H2,1H3/t3-/m1/s1

Upstream product

• 5950-34-5 methyl aziridine-2-carboxylate 
• 160233-42-1 (2R)-1-tritylaziridine-2-carboxylic acid methyl ester 
• 2104-89-4 D-serine methyl ester 
• 86852-11-1 diethoxyltriphenylphosphorane 
• 5874-57-7 R-(-)-serine methyl ester hydrochloride 
• 154632-86-7 O₁-benzyl-O₂-methyl-(2R)-aziridine-1,2-dicarboxylate 

Downstream Products

• 154632-86-7 O₁-benzyl-O₂-methyl-(2R)-aziridine-1,2-dicarboxylate 
• 1021495-51-1 methyl (R)-N-(p-nitrobenzenesulfonyl)aziridine-2-carboxylate 
• 1239355-46-4 1-tert-Butyl 2-Methyl (R)-Aziridine-1,2-dicarboxylate 
• 155976-02-6 methyl (2R)-N-(4-methylphenyl)sulfonylaziridine-2-carboxylate 

Relevant articles and documents

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Studies on the synthesis of orthogonally protected azalanthionines, and of routes towards β-methyl azalanthionines, by ring opening of N-activated aziridine-2-carboxylates

Orthogonally protected azalanthionines were successfully synthesised by the ring-opening of N-activated aziridine-2-carboxylates with protected diaminopropanoic acids (DAPs). The required DAPs were also prepared by ring-opening of N-activated aziridine-2-carboxylates with para- methoxybenzylamine, but it was found that the choice of aziridine protecting groups dictated both the success of the reaction as well as the regioselectivity of the isolated products. Attempts to extend the methodology to the preparation of the more sterically demanding β-methyl azalanthionines have, so far, been unsuccessful.

Synthesis of orthogonally protected azalanthionines (lanazanines) by sequential ring-opening of N-substituted aziridine 2-carboxylates

Orthogonally protected azalanthionines (lanazanines, 4-azadiaminopimelic acids or β-aminoalaninoalanines) have been synthesised in good yields by the ring-opening of N-protected aziridine 2-carboxylates with suitably protected diaminopropanoic acids (DAPs

Discovery of a new class of glucosylceramide synthase inhibitors

A novel series of potent inhibitors of glucosylceramide synthase are described. The optimization of biochemical and cellular potency as well as ADME properties led to compound 23c. Broad tissue distribution was obtained following oral administration to mice. Thus 23c could be another useful tool compound for studying the effects of GCS inhibition in vitro and in vivo.

The structure?activity relationship of the 3-Oxy site in the anticonvulsant (R)- N -benzyl 2-acetamido-3-methoxypropionamide

Lacosamide ((R)-N-benzyl 2-acetamido-3-methoxypropionamide, (R)-1) is a low molecular weight anticonvulsant recently introduced in the United States and Europe for adjuvant treatment of partial-onset seizures in adults. In this study, we define the structure?activity relationship (SAR) for the compound's 3-oxy site. Placement of small nonpolar, nonbulky substituents at the 3-oxy site provided compounds with pronounced seizure protection in the maximal electroshock (MES) seizure test with activities similar to (R)-1. The anticonvulsant activity loss that accompanied introduction of larger moieties at the 3-oxy site in (R)-1 was offset, in part, by including unsaturated groups at this position. Our findings were similar to a recently reported SAR study of the 4?-benzylamide site in (R)-1 (J. Med. Chem. 2010, 53, 1288 ?1305). Together, these results indicate that both the 3-oxy and 4?-benzylamide positions in (R)-1 can accommodate nonbulky, hydrophobic groups and still retain pronounced anticonvulsant activities in rodents in the MES seizure model.

Proteomic searches comparing two (R)-lacosamide affinity baits: An electrophilic arylisothiocyanate and a photoactivated arylazide group

We have advanced a novel strategy to search for lacosamide ((R)-1) targets in the brain proteome where protein binding is expected to be modest. Our approach used lacosamide agents containing "affinity bait" (AB) and "chemical reporter" (CR) units. The affinity bait moiety is designed to irreversibly react with the target, and the CR group permits protein detection and capture. In this study, we report the preparation and evaluation of (R)-N-(4-azido)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-3) and show that this compound exhibits potent anticonvulsant activities in the MES seizure model in rodents. We compared the utility of (R)-3 with its isostere, (R)-N-(4-isothiocyanato)benzyl 2-acetamido-3-(prop-2-ynyloxy)propionamide ((R)-2), in proteomic studies designed to identify potential (R)-1 targets. We showed that despite the two-fold improved anticonvulsant activity of (R)-3 compared with (R)-2, (R)-2 was superior in revealing potential binding targets in the mouse brain soluble proteome. The difference in these agents' utility has been attributed to the reactivity of the affinity baits (i.e., (R)-2: aryl isothiocyanate moiety; (R)-3: photoactivated aryl azide intermediates) in the irreversible protein modification step, and we conclude that this factor is a critical determinant of successful target detection where ligand (drug) binding is modest. The utility of (R)-2 and (R)-3 in in situ proteome studies is explored.