65491-01-2

Usage

Uses

Used in Pharmaceutical Industry:
(2R)-2-(Benzylamino)propanoic acid is used as a precursor in the synthesis of various drugs and pharmaceutical compounds, contributing to the development of new medications and therapies.
Used in Research Laboratories:
(2R)-2-(Benzylamino)propanoic acid is used as a building block for the creation of new molecules and for studying the effects of chiral compounds on biological systems, aiding in the advancement of scientific knowledge and potential applications.
Used in Drug Delivery Systems Development:
(2R)-2-(Benzylamino)propanoic acid may have potential applications in the development of novel drug delivery systems, potentially improving the efficacy and targeting of pharmaceutical agents.
Used in Biochemical Assays:
(2R)-2-(Benzylamino)propanoic acid may serve as a component in biochemical assays, facilitating research and analysis in various biological and chemical processes.

Upstream product

• 598-72-1 2-Bromopropionic acid 
• 100-46-9 benzylamine 
• 32644-15-8 (S)-2-bromopropanoic acid 
• 75995-60-7 1,4-dibenzyl-3,6-dimethyl-2,5-dioxopiperazine 
• 7647-01-0 hydrogenchloride 
• 64-19-7 acetic acid 
• 64892-53-1 N-benzylalanine ethyl ester 
• 100-52-7 benzaldehyde 
• 302-72-7 rac-Ala-OH 
• 100-44-7 benzyl chloride 
• 622-79-7 benzyl azide 
• 127-17-3 2-oxo-propionic acid 
• 1634-04-4 tert-butyl methyl ether 
• 159721-22-9 N-benzyl-alanine methyl ester 

Downstream Products

• 19460-84-5 N-benzyl-N-acetylalanine 
• 20135-15-3 N-ethylidenebenzylamine N-oxide 
• 7585-47-9 N-benzyl-(S)-alanine 
• 106150-53-2 Cu((C₆H₅CH₂)NHCH(CH₃)COO)2(H₂O)2 
• 101692-94-8 (rac)-N-benzyl-N-methylalanine 
• 1012787-10-8 3-benzyl-1,2-dimethyl-5-phenylthio-1,2,3,4-tetrahydropyrimido[4,5-d]pyrimidine 
• 1012787-09-5 3-ethyl-1-methyl-2-phenyl-5-phenylthio-1,2,3,4-tetrahydropyrimido[4,5-d]pyrimidine 
• 1012787-00-6 1-allyl-3-ethyl-2-phenyl-5-phenylthio-1,2,3,4-tetrahydropyrimido[4,5-d]pyrimidine 
• 1012787-01-7 1-allyl-3-benzyl-2-methyl-5-phenylthio-1,2,3,4-tetrahydropyrimido[4,5-d]pyrimidine 
• 31022-10-3 N-benzyl-L-alanine methyl ester 
• 188777-45-9 (S)-2-{1-benzyl-2-[(tert-butoxy)carbonyl]hydrazino}propanoic acid 
• 159999-80-1 N-benzyl-N-Boc-L-alanine 

Relevant academic research and scientific papers

PROCESS FOR THE PREPARATION OF CYCLOPROPYLDIKETOPIPERAZINES AND OF A KEY INTERMEDIATE OF DS-5272

Object of the present invention is an improved process for the preparation of cyclopropyldiketopiperazines and thereof key intermediates.

Tuning of protease resistance in oligopeptides through: N -alkylation

N-Methylation of amino acids is an effective way to create protease resistance in both natural and synthetic peptides. However, alkyl substituents other than N-methyl have not been extensively studied. Here, we prepare and examine a series of N-substituted peptides in which the size and length of the alkyl group is modulated. These design insights provide a unique and modular handle for tuning proteolysis in oligopeptides.

Controlling Plasma Stability of Hydroxamic Acids: A MedChem Toolbox

Hydroxamic acids are outstanding zinc chelating groups that can be used to design potent and selective metalloenzyme inhibitors in various therapeutic areas. Some hydroxamic acids display a high plasma clearance resulting in poor in vivo activity, though they may be very potent compounds in vitro. We designed a 57-member library of hydroxamic acids to explore the structure-plasma stability relationships in these series and to identify which enzyme(s) and which pharmacophores are critical for plasma stability. Arylesterases and carboxylesterases were identified as the main metabolic enzymes for hydroxamic acids. Finally, we suggest structural features to be introduced or removed to improve stability. This work thus provides the first medicinal chemistry toolbox (experimental procedures and structural guidance) to assess and control the plasma stability of hydroxamic acids and realize their full potential as in vivo pharmacological probes and therapeutic agents. This study is particularly relevant to preclinical development as it allows obtaining compounds equally stable in human and rodent models.

Catalytic enantioselective synthesis of N,Cα,Cα-trisubstituted α-amino acid derivatives using 1H-imidazol-4(5H)-ones as key templates

Abstract 1H-Imidazol-4(5H)-ones are introduced as novel nucleophilic α-amino acid equivalents in asymmetric synthesis. These compounds not only allow highly efficient construction of tetrasubstituted stereogenic centers, but unlike hitherto known templates, provide direct access to N-substituted (alkyl, allyl, aryl) α-amino acid derivatives. A BB method: 1H-imidazol-4(5H)-ones serve as effective and easily available α-amino acid surrogates for the catalytic and highly diastereo- and enantioselective direct construction of N-substituted quaternary α-amino acid derivatives. The reaction is catalyzed by a Br?nsted base (BB) and proceeds with different Michael acceptors. EWG=electron-withdrawing group.

Structure-Activity Relationships of the Peptide Kappa Opioid Receptor Antagonist Zyklophin

The dynorphin (Dyn) A analogue zyklophin ([N-benzyl-Tyr1-cyclo(d-Asp5,Dap8)]dynorphin A(1-11)NH2) is a kappa opioid receptor (KOR)-selective antagonist in vitro, is active in vivo, and antagonizes KOR in the CNS

Concise, stereodivergent and highly stereoselective synthesis of cis-and trans-2-substituted 3-hydroxypiperidines-development of a phosphite-driven cyclodehydration

A concise (5 to 6 steps), stereodivergent, highly diastereoselective (dr up to >19:1 for both stereoisomers) and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, a core motif in numerous bioactive compounds, is presented. This sequence allowed an efficient synthesis of the NK-1 inhibitor L-733,060 in 8 steps. Additionally, a cyclodehydration-realizing simple triethylphosphite as a substitute for triphenylphosphine is developed. Here the stoichiometric oxidized P(V)-byproduct (triethylphosphate) is easily removed during the work up through saponification overcoming separation difficulties usually associated to triphenylphosphine oxide.

Efficient, stereodivergent access to 3-piperidinols by traceless P(OEt)3 cyclodehydration

A stereodivergent and highly diastereoselective (dr up to >19:1 for both isomers), step economic (5-6 steps), and scalable synthesis (up to 14 g) of cis- and trans-2-substituted 3-piperidinols, the core motif of numerous bioactive compounds, providing efficient access to the NK-1 inhibitor L-733,060 is presented. Additionally, a "traceless" (referring to the simplified byproduct separation) cyclodehydration realizing simple P(OEt)3 as a substitute for PPh3 is developed.

A Dieckmann cyclization route to piperazine-2,5-diones

Piperazine-2,5-diones are formed by Dieckmann cyclization (NaH, THF) of substructures of the type CH2-N(R)C(O)CH2N(R′) CO2Ph in which the terminal methylene (CH2) that is adjacent to nitrogen closes onto the carbonyl group of the phenyl carbamate unit at the other end of the chain. R and R′ are alkyl groups, and the terminal methylene is activated by a ketone carbonyl, a nitrile, an ester, or a phosphoryl group. The starting materials are assembled by standard acylation and oxidation processes, starting from a β-(alkylamino)alcohol, an (alkylamino)acetonitrile, an (alkylamino) ester, or an (alkylamino)methyl phosphonate.

Thermophysical study of several α- And β-amino acid derivatives by differential scanning calorimetry (DSC)

The present study reports a differential scanning calorimetry (DSC) study of the amino acids sarcosine [CAS Registry No. 107-97-1], α-alanine (dl) [CAS Registry No. 302-72-7], β-alanine [CAS Registry No. 107-95-9], N-benzyl-α-alanine (dl) [CAS Registry No

Resolution of racemic N-benzyl α-amino acids by liquid-liquid extraction: A practical method using a lipophilic chiral cobalt(III) salen complex and mechanistic studies

The efficient resolution of racemic N-benzyl α-amino acids (N-Bn-AA) has been achieved by a liquid-liquid extraction process using the lipophilic chiral salen-cobalt(III) complex [CoIII(3)(OAc)]. As a result of the resolution by extraction, one enantiomer (S) of the N-benzyl α-amino acid predominated in the aqueous phase, while the other enantiomer (R) was driven into the organic phase by complexation to cobalt. The complexed amino acid (R) was then quantitatively released by a reductive (CoIII→Co II) counter-extraction with aqueous sodium dithionite or L-ascorbic acid in methanol. The reductive cleavage allowed to recover the [Co II(3)] complex in good yield, which could be easily re-oxidized to [CoIII(3)(OAc)] with air/AcOH and reused with essentially no loss of reactivity and selectivity. Investigation on the nitrogen substitution indicates that the presence of a single benzyl group on the amino acid nitrogen is important to obtain high enantioselectivity in the extraction process. The kinetic vs. thermodynamic nature of the resolution process was also investigated with an enantiomeric exchange experiment, which shows that the liquid-liquid extraction with [CoIII(3)-(OAc)] is an equilibrium process operating under thermodynamic control. In the absence of a suitable crystal structure of the [CoIII(3)(N-Bn-AA)] complexes, computational and spectroscopic studies were used to investigate how the N-benzyl α-amino acids are accommodated in the "binding pocket" of the chiral cobalt complex. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.