144494-72-4

Usage

Uses

Used in Pharmaceutical Industry:
(S)-3-Amino-3-phenyl propionic acid methylester HCl is used as an intermediate in the synthesis of pharmaceuticals for its potential role in the development of new drugs. Its unique structure may contribute to the creation of novel therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-3-Amino-3-phenyl propionic acid methylester HCl serves as a building block for the construction of more complex organic molecules. Its chiral nature and functional groups make it a valuable component in the synthesis of various organic compounds.
Used in Research and Development:
(S)-3-Amino-3-phenyl propionic acid methylester HCl is utilized in research and development for studying its properties and potential applications. Its unique structure may offer insights into new chemical reactions and mechanisms, contributing to the advancement of scientific knowledge.

InChI:InChI=1/C10H13NO2.ClH/c1-13-10(12)7-9(11)8-5-3-2-4-6-8;/h2-6,9H,7,11H2,1H3;1H/t9-;/m0./s1

Upstream product

• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 67-56-1 methanol 
• 100-52-7 benzaldehyde 
• 1174169-22-2 3-(2-methyl-propane-2-sulfinylamino)-3-phenyl-propionic acid methyl ester 

Downstream Products

• 51031-37-9 3-isocyanato-3-phenyl-propionic acid methyl ester 
• 127022-85-9 3-Amino-N-hexyl-3-phenyl-propionamide; hydrochloride 
• 124082-23-1 3-(2-Ethoxycarbonyl-acetylamino)-3-phenyl-propionic acid methyl ester 
• 144426-37-9 3-Phenyl-3-{2-[4-((E)-styryl)-phenoxy]-acetylamino}-propionic acid methyl ester 
• 144426-41-5 3-(2-{4-[(E)-2-(4-Chloro-phenyl)-vinyl]-phenoxy}-acetylamino)-3-phenyl-propionic acid methyl ester 
• 144426-40-4 3-Phenyl-3-{2-[4-((E)-styryl)-phenoxy]-propionylamino}-propionic acid methyl ester 
• 174635-62-2 (R,S)-N-[α-(methoxycarbonylmethyl)benzyl]-2-phenylquinoline-4-carboxamide 
• 88831-32-7 3-(3-Oxo-3-phenyl-propylamino)-3-phenyl-propionic acid methyl ester; hydrochloride 
• 329911-77-5 methyl tert-butoxycarbonyl-glycyl-D,L-β-phenyl-β-alaninate 
• 7032-62-4 3-phenyl-3-piperidinopropionic acid methyl ester 
• 97-02-9 2,4-Dinitroanilin 
• 656808-19-4 (RS)-(+/-)-N-(2-(methoxycarbonyl)-1-phenylethyl)malonamic acid methyl ester 
• 807627-84-5 N-[4-(N-Boc-isoindolin-5-yl)amino-4-oxobutyryl]-β-phenyl-β-alanine methyl ester 
• 257861-50-0 3-tert-butoxycarbonylamino-3-phenylpropionic acid methyl ester 

Relevant academic research and scientific papers

Transition Metal-Free N-Arylation of Amino Acid Esters with Diaryliodonium Salts

A transition metal-free approach for the N-arylation of amino acid derivatives has been developed. Key to this method is the use of unsymmetric diaryliodonium salts with anisyl ligands, which proved important to obtain high chemoselectivity and yields. The scope includes the transfer of both electron deficient, electron rich and sterically hindered aryl groups with a variety of different functional groups. Furthermore, a cyclic diaryliodonium salt was successfully employed in the arylation. The N-arylated products were obtained with retained enantiomeric excess.

Highly enantioselective enzymatic resolution of aromatic β-amino acid amides with Pd-catalyzed racemization

The kinetic resolution of an aromatic β-amino acid amide 3a-d via N-acylation was explored with two lipases, Candida antarctica lipase A (CALA) and Pseudomonas stutzeri lipase (PSL). The PSL-catalyzed resolution proceeded with excellent enantioselectivity

Synthesis, in vitro and in vivo biological evaluation, docking studies, and structure-activity relationship (SAR) discussion of dipeptidyl boronic acid proteasome inhibitors composed of β-amino acids

A series of novel dipeptidyl boronic acid proteasome inhibitors composed of β-amino acids were synthesized, in vitro and in vivo biologically evaluated, and theoretically modeled for the first time. From the screened racemic compounds in enzyme, 4i was the most active. The IC50 value of its pure enantiomer 4q was 9.6 nM, 36-fold more active than its isomer 4p and as active as the marketed bortezomib in inhibiting human 20S proteasome. This candidate also showed good activities with IC50 values nearly less than 5 μM against several human solid and hematologic tumor cell lines. Safety evaluation in vivo with zebrafish and Sprague-Dawley (SD) rats showed that the candidate 4q was less toxic than bortezomib. Pharmacokinetic profiles suggested candidate 4q showed a more plasma exposure and longer half-life than bortezomib. Docking results indicated that 4q nearly interacted with 20S proteasome in a similar way as bortezomib.

BETA-AMINO ACID DERIVATIVES FOR TREATMENT OF DIABETES

Novel heterocyclic compounds of the Formula (I) in which R1, R2, R2', R2', R3, R4, R5, R6, R7 and R8 have the meanings indicated in Claim 1, are activators of glucokinase and can be used for the prevention and/or treatment of Diabetes Typ 1 and 2, obesity, neuropathy and/or nephropathy.

β-amino acids to piperidinones by petasis methylenation and acid-induced cyclization

(Chemical Equation Presented) Ester-imine derivatives of β-amino acids were methylenated with dimethyltitanocene under microwave irradiation and the resulting enol ethers cyclized with Broensted acid or triisopropylaluminium to give 2,6-syn-disubstituted

Synthesis and physicochemical characterization of new C-functionalized derivatives of the gadolinium(III) complex with 3,6,10-tris(carboxymethyl)-3,6, 10-triazadodecanedioic acid (H5ttda) exhibiting fast water exchange - Potential paramagnetic reporters for molecular imaging

To confirm the observation that [Gd(ttda)] derivatives have a significantly shorter residence time τM of the coordinated H2O molecule than [Gd(dtpa)], four new C-functionalized [Gd(ttda)] complexes, [Gd(4-Me-ttda)] (1), [Gd(4-Ph-ttda)] (2), [Gd(9-Me-ttda)] (3), and [Gd(9-Ph-ttda)] (4), were prepared and characterized (H5ttda = 3,6,10-tris(carboxymethyl)-3,6,10-triazadodecanedioic acid; H5dtpa = 3,6,9-tris(carboxymethyl)-3,6,9-triazaundecanedioic acid). The temperature dependence of the proton relaxivity for these complexes at 0.47 T and of the 17O transverse relaxation rate of H217O at 7.05 T confirm that the proton relaxivity is not limited by the H 2O-exchange rate. The residence time of the H2O molecules in the first coordination sphere of the gadolinium complexes at 310 K, as calculated from 17O-NMR data, is 13, 43, 2.9, and 56 ns for 1, 2, 3, and 4, respectively. At 310 K, the longitudinal relaxivity of 2 is higher than for the parent compound [Gd(ttda)] and the other complexes of the series. The stability of the new compounds was studied by transmetallation with Zn 2+ ions. All the new complexes are more stable than the parent compound [Gd(ttda)].

Ruthenium-catalyzed asymmetric epoxidation of olefins using H 2O2, part I: Synthesis of new chiral N,N,N,-tridentate pybox and pyboxazine ligands and their ruthenium complexes

The synthesis of chiral tridentate N,N,N-pyridine-2.6-bisoxazolines 3 (pyhox ligands) and N,N,N-pyridine-2.6-bisoxazines 4 (pyboxazine ligands) is described in detail. These novel ligands constitute a useful tool-box for the application in asymmetric catalysis. Compounds 3 and 4 are conveniently prepared by cyclization of enantiomerically pure α- or β-amino al cohols with dimethyl pyridine-2,6-dicarboximidate. The corresponding ruthenium complexes are efficient asymmetric epoxidation catalysts and have been prepared in good yield and fully char acterized by spectroscopic means. Four of these ruthenium complexes have been characterized by X-ray crystallography. For the first time the molecular structure of a pyboxazine complex (2,6-bis-[(4S)-4-phenyl-5,6- dihydro-4H-[1,3]oxazinyl]pyridine)(pyridine-2,6-dicarboxylate)ruthenium (S)-2aa, is presented.

Synthesis and antiaggregation activity of a new RGDF peptidomimetic

A new RGDF peptidomimetic, [4-oxo-4-(pyperazin-1-yl)butyryl]glycyl-D,L-β-phenyl-β-alanine was synthesized. The arginyl mimetic used was the 4-oxo-4-(piperazin-1-yl)butanoic acid residue, and the Asp-Phe chain is replaced by a β-phenyl-β-alanine residue. The synthesized pseudopeptide showed ability to inhibite ADF-induced thrombocyte aggregation in a thrombocyte-rich rat blood plasma (IC50 8.7 × 10-9 M).

Synthesis and CNS activity of new 3-amino-3-arylpropionic acid derivatives

The synthesis of new analogues of methylphenidate and modafinil, derived from 3-amino-3-arylpropionic acids, is described. Central pharmacological properties were studied in mice.

X-ray crystallographic study of substituted perhydropyrimidinones. Extreme changes in ring conformation

X-ray crystal structures of 20 differently substituted perhydropyrimidin-4-ones are presented. Analysis of these data reveal a remarkable conformational sensitivity of a six-membered ring to substitution. Thus half-chair, envelope, boat, twist-boat, and intermediate conformations are found for the six-membered heterocycle, providing evidence for a relatively fiat conformational energy surface in this ring. Interpretation of the preferred conformations is advanced in terms of steric interactions among substituents and, in some cases, as the result of particular conformational (A1.3 strain, anomeric) effects.