197020-60-3

Usage

Molecular Structure

The compound has an aziridine ring with a carboxyl group, a 2-methyl group, and a 1,1-dimethylethyl ester group.

Stereochemistry

The compound has a specific (2S) stereochemical configuration, which is important for its applications in chiral drugs and organic synthesis.

Reactivity

The compound is highly reactive, which makes it useful as an intermediate in the synthesis of various pharmaceuticals and agrochemicals.

Versatility

The compound has a wide range of applications, including the production of polymers, resins, and as a reagent in chemical reactions.

Toxicity

The compound is toxic and potentially hazardous, which requires strict regulation and control of its production and use.

Usage

Commonly used in the pharmaceutical and chemical industries as an intermediate in the synthesis of various pharmaceuticals and agrochemicals, as well as in the production of polymers, resins, and as a reagent in chemical reactions.

Chirality

The (2S) enantiomer of the compound has a specific stereochemical configuration, which is useful in the production of chiral drugs and as a chiral building block in organic synthesis.

Regulation

The compound is regulated and strictly controlled due to its toxic and potentially hazardous nature.

Upstream product

• 79069-13-9 (S)-2-t-butoxycarbonylaminopropan-1-ol 
• 126301-16-4 (2S)-2-[(tert-butoxycarbonyl)amino]propyl methanesulfonate 
• 24424-99-5 di-tert-butyl dicarbonate 
• 15761-38-3 L-N-Boc-Ala 

Downstream Products

• 1142923-88-3 C₁₄H₁₉BrClNO₂ 
• 1206475-87-7 (2S)-1-(3',5'-dimethoxyphenyl)-N-(tert-butoxycarbonyl)-2-aminopropane 
• 1414377-85-7 (2R,3S)-tert-butyl 3-methylaziridine-2-carboxylate 
• 1356349-85-3 tert-butyl [(2S)-1-cyclohexylpropan-2-yl]carbamate 

Relevant academic research and scientific papers

An improved process for the N-alkylation of indoles using chiral N-protected 2-methylaziridines

An improved process for the N-alkylation of indoles using N-protected homochiral aziridines has been developed. This procedure allows reduced quantities of homochiral starting material to be used and leads to improved overall yields and operability.

Aziridine-2-carboxaldehyde dimers undergo homo-Ugi 4-component-5-center reactions

Dimeric α-aziridine aldehydes have been used as the aldehyde component in Ugi and Passerini reactions. The highly reactive mixed anhydride intermediate is subject to nucleophilic attack by the aziridine, leading to homo-Ugi' β-acylaziridinyl-α-aminoamides. The products can be readily transformed into substituted lactones. Georg Thieme Verlag Stuttgart ? New York.

HETEROCYCLIC SULFONAMIDES AS INHIBITORS OF TRANSFER RNA SYNTHETASE FOR USE AS ANTIBACTERIAL AGENTS

The present invention provides aromatic sulphonamides as tRNA synthetase inhibitors and process for their synthesis, pharmaceutical composition and method for treatment. Compounds disclosed can be used as antibacterial agents for the treatment or prevention of conditions caused by or contributed by aerobic and anaerobic Gram-positive pathogens, more particularly against bacterium, for example Staphylococcus, Enterococci and Streptococci. Compounds disclosed are used in particular for the treatment of skin and soft tissue infection, Formula (I)

Total synthesis of the N,C-coupled naphthylisoquinoline alkaloids ancistrocladinium A and B and related analogues

The N,C-coupled naphthyldihydroisoquinoline alkaloids ancistrocladinium A (3) and B (4), which possess an unprecedented iminium-aryl axis and show high in vitro antileishmanial activities, have been synthesized via a short sequence of eight linear steps, without the need of protecting groups. Key steps were a Buchwald-Hartwig amination and a Bischler-Napieralski cyclization, preferentially leading to the naturally predominant M-atropo-diastereomer in the case of 3, while the N,C-axis is configurationally semistable in 4. The highly convergent first access to this type of alkaloids will now facilitate the preparation of structural analogues for structure-activity relationship studies. Its general applicability was shown by the preparation of the sterically even more congested, as yet unnatural N,3′- and N,1′-coupled analogues, ancistrocladinium C (5) and D (6).

Aminoalkylbenzofurans as serotonin (5-HT(2c)) agonists

The present invention provides serotonergic aminoalkylbenzofurans of Formula (I): where R, R1, R2, R3, R4, R4′, R5, R5′, and R12 are as described in the specification.

5-HT2C receptor agonists for the treatment of obesity. Biological and chemical adventures

Obesity is a major risk factor in the development of conditions such as hypertension, hyperglycemia, dyslipidemia, coronary artery disease and cancer. There is increasing evidence suggesting an important role for the 5-HT 2C receptor in appetite control. Collaboration between F. Hoffmann-La Roche Ltd and Vernalis Research Ltd has allowed rapid construction of a solid structure-activity relationship around a pyrroloindole core. A one-pot Sonogashira reaction followed by nucleophilic double cyclisation allows an elegant and expedient route to this central motif. Introduction of a (2S)-aminopropyl group in place of the aminoethyl endogenous ligand side-chain enhanced the affinity at the 5-HT2C receptor and reduced affinity towards monoamine oxidase enzymes (MAO). Sulfamidate reagents were found to be very effective for the introduction of the 2-aminopropyl moiety in a stereoselective manner. The substitution at position 5 (indole numbering) was found to be crucial for both affinity and selectivity. Pyrroloindoles bearing an alkoxyether in this position exhibit promising pharmacokinetic parameters in rodent and significant reduction of food intake, after per os application.

A Convenient One-Pot Conversion of N-Boc-β-Aminoalcohols into N-Boc-Aziridines

This paper describes an efficient single step transformation of chiral N-protected β-amino alcohols into appropriate aziridines.

A convenient synthesis of chiral N-Boc-amino ethers as potential peptide bond surrogate units

Boron triflouride etherate and zinc triflate have been found to be effective catalysists for the synthetic route to chiral N-Boc-amino ethers via a Lewis acid-catalyzed ring-opening of N-acyl aziridines, derived from chiral amino acids.