405175-79-3

Usage

Uses

Used in Pharmaceutical Research and Development:
(R)-4-N-CBZ-PIPERAZINE-2-CARBOXYLIC ACID METHYL ESTER is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to contribute to the creation of enantiomerically pure compounds. This is significant as the biological activity of enantiomers can differ, affecting the efficacy and safety of drugs.
Used in Organic Synthesis:
In the field of organic synthesis, (R)-4-N-CBZ-PIPERAZINE-2-CARBOXYLIC ACID METHYL ESTER serves as a versatile reagent and building block for the development of complex organic molecules, including those with potential applications in material science and specialty chemicals.
Used in Agrochemical Development:
(R)-4-N-CBZ-PIPERAZINE-2-CARBOXYLIC ACID METHYL ESTER is utilized as a component in the design and synthesis of agrochemicals, such as pesticides and herbicides, where its chiral properties can be leveraged to enhance the selectivity and effectiveness of these compounds in agricultural applications.
Used in the Production of Fine Chemicals:
(R)-4-N-CBZ-PIPERAZINE-2-CARBOXYLIC ACID METHYL ESTER is also used as a precursor in the manufacture of fine chemicals, which are high-purity, high-value chemicals used in various industries, including fragrances, flavors, and cosmetics, capitalizing on its ability to form specific enantiomers with desired properties.

InChI:InChI=1/C14H18N2O4/c1-19-13(17)12-9-16(8-7-15-12)14(18)20-10-11-5-3-2-4-6-11/h2-6,12,15H,7-10H2,1H3/t12-/m1/s1

Upstream product

• 67-56-1 methanol 
• 138775-02-7 (2R)-4-[(benzyloxy)carbonyl]-1-[(tert-butoxy)carbonyl]piperazine-2-carboxylic acid 
• 129799-11-7 1-benzyl 3-methyl piperazine-1,3-dicarboxylate 
• 126330-91-4 Methyl (R)-6-oxopiperazine-2-carboxylate 
• 501-53-1 benzyl chloroformate 
• 126330-92-5 3-amino-N-[(benzyloxy)carbonyl]-D-alanine methyl ester 

Downstream Products

• 278790-00-4 piperazine-1,2,4-tricarboxylic acid 4-benzyl ester 1-tert-butyl ester 2-methyl ester 
• 405175-82-8 (R)-4-[Ethoxy-(4-methoxy-phenyl)-phosphinoyl]-piperazine-1,3-dicarboxylic acid 1-benzyl ester 3-methyl ester 
• 954410-00-5 methyl 3-[(3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)piperazin-1-yl]-1-naphthoate 
• 954409-59-7 ((2R)-1-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazin-2-yl)methyl acetate 
• 954409-61-1 benzyl (3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}-3-(hydroxymethyl)-piperazine-1-carboxylate 
• 954409-62-2 benzyl (3R)-3-[(acetyloxy)methyl]-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazine-1-carboxylate 
• 954409-60-0 1-benzyl 3-methyl (3R)-4-{[1-(3-ethoxyphenyl)-2-(4-methylphenyl)-1H-imidazol-4-yl]carbonyl}piperazine-1,3-dicarboxylate 

Relevant academic research and scientific papers

Solid-phase synthesis and biological evaluation of piperazine-based novel bacterial topoisomerase inhibitors

There is an emerging global need for new and more effective antibiotics against multi-resistant bacteria. This situation has led to massive industrial investigations on novel bacterial topoisomerase inhibitors (NBTIs) that target the vital bacterial enzym

KINETIC RESOLUTION OF CHIRAL AMINES

The present invention refers to a method for the kinetic resolution of a chiral primary or secondary amine by treating the amine with a chiral, hydroxamic acid derived reagent of the formula (I). These chiral reagents are particularly useful for the kinetic resolution of cyclic amines and may be generated in situ in the presence of an N-heterocyclic carbene, thus allowing for a catalytic reaction.

Expanded substrate scope and catalyst optimization for the catalytic kinetic resolution of N-heterocycles

The scope, reactivity, and selectivity of the chiral hydroxamic acid-catalyzed kinetic resolution of chiral amines are improved by a new catalyst structure and a more environmentally friendly reaction protocol. In addition to increasing selectivity across all substrates, these conditions make possible the resolution of N-heterocycles containing lactams or other basic functional groups that can inhibit the catalyst.

Potent, orally active GPIIb/IIIa antagonists containing a nipecotic acid subunit. Structure-activity studies leading to the discovery of RWJ-53308

Although intravenously administered antiplatelet fibrinogen receptor (GPIIb/IIIa) antagonists have become established in the acute-care clinical setting for the prevention of thrombosis, orally administered drugs for chronic use are still under development. Herein, we present details from our exploration of structure-activity surrounding the prototype fibrinogen receptor antagonist RWJ-50042 (racemate of 1), which was derived from a unique approach involving the γ-chain of fibrinogen (Hoekstra et al. J. Med. Chem. 1995, 38, 1582). Our analogue studies culminated in the discovery of RWJ-53308 (2), a potent, orally active GPIIb/IIIa antagonist. To progress from RWJ-50042 to a suitable candidate for clinical development, we conducted a series of optimization cycles that employed solid-phase parallel synthesis for the rapid, efficient preparation of nearly 250 analogues, which were assayed for fibrinogen receptor affinity and inhibition of platelet aggregation induced by four different activators. This strategy produced several promising analogues for advanced study, including 3-(3,4- methylenedioxybenzene)-β-amino acid analogue 3 (significant improved in vivo potency) and 3-(3-pyridyl)-β-amino acid 2 (significantly improved potency, oral absorption, and duration of action). In dogs, 2 displayed significant ex vivo antiplatelet activity on oral administration at 1.0 mg/kg, 16% systemic oral bioavailability, minimal metabolic transformation, and an excellent safety profile. Additionally, 2 was found to be efficacious in three in vivo thrombosis models: canine arteriovenous (AV) shunt (0.01-0.1 mg/kg, iv), guinea pig photoactivation-induced injury (0.3-3 mg/kg, iv), and guinea pig ferric chloride-induced injury (0.3-1 mg/kg, iv). On the basis of its noteworthy preclinical data, RWJ-53308 (2) was selected for clinical evaluation.