3082-68-6

Usage

Uses

Used in Pharmaceutical Industry:
(R)-3-Amino-3-phenylpropionic acid ethyl ester is used as an intermediate in the three-step synthesis of β-amino acids. These β-amino acids are essential building blocks for the development of various pharmaceutical compounds, including those with potential therapeutic applications.
Used in Microbial Production:
In the field of biotechnology, (R)-3-Amino-3-phenylpropionic acid ethyl ester is utilized in the microbial production of β-phenylalanine ethyl esters. This process involves the use of microorganisms to convert precursor compounds into the desired product, which can then be used for further synthesis or as a final product in the pharmaceutical or chemical industries.

Upstream product

• 42201-84-3 1-ethoxy-1-(tert-butyldimethylsilyloxy)ethene 
• 253665-35-9 (1S,2R,4R,S_S)-7,7-dimethyl-N-(phenylmethylene)-2-(trimethylsilyloxy)bicyclo[2.2.1]heptane-1-methanesulfinamide 
• 340188-50-3 (R)-3-amino-3-phenylpropionic acid ethyl ester hydrochloride 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 94-02-0 ethyl 3-oxo-3-phenylpropionate 
• 14191-09-4 ethyl (2Z)-3-(benzylamino)-3-phenylacrylate 
• 1282538-74-2 ethyl 3-(benzylamino)-3-phenylpropanoate 
• 29754-04-9 ethyl 3-amino-3-phenylpropanoate hydrochloride 
• 893395-89-6 (R)-3-([(R)-2-amino-2-oxo-1-phenylethyl]amino)-3-phenylpropionic acid ethyl ester hydrochloride 
• 650601-35-7 ethyl 3-amino-3-phenylacrylate methanesulfonate 
• 33831-72-0 ethyl 3-amino-3-phenylprop-2-enoate 
• 100-52-7 benzaldehyde 
• 3646-50-2 3-Amino-3-phenylpropionic acid 
• 680594-91-6 ((R)-2-Benzyloxy-1-phenyl-ethyl)-[1-phenyl-meth-(E)-ylidene]-amine 

Downstream Products

• 3082-70-0 (S)-N-Salicyliden-<3-phenyl-3-amino-propionsaeureaethylester> 
• 170564-98-4 (R)-3-amino-3-phenyl-1-propanol 
• 614-19-7 (R)-3-phenyl-3-aminopropionic acid 
• 2021-28-5 ethyl dihydrocinnamate 
• 6335-76-8 3-amino-3-phenylpropionic acid ethyl ester 
• 854689-11-5 salt of (R)-benzyloxycarbonylphenylalanine and (R)-3-amino-3-phenylpropionic acid ethyl ester 
• 854689-16-0 salt of (R)-benzyloxycarbonylamino-tert-leucine and (R)-3-amino-3-phenylpropionic acid ethyl ester 
• 36567-72-3 (S)-3-hydroxy-3-phenylpropanoic acid 
• 621-82-9 Cinnamic acid 

Relevant academic research and scientific papers

Highly enantioselective one-pot, three-component imino-reformatsky reaction

(Chemical Equation Presented) A key to molecular diversity is the preparation of new frameworks in multi-component condensations of three or more reactants. A new highly enantioselective one-pot, three-component, nickel-catalyzed, imino-Reformatsky reacti

Lead tetraacetate cleavage of chiral phenylglycinol derived secondary amines without racemization

Diastereomerically enriched N-(1,1-disubstituted methyl)(2'-hydroxy-1'-phenylethyl)amines were oxidatively converted to enantiomerically enriched primary disubstituted methylamines in excellent yields without racemization, using an improved lead tetraacetate (LTA) procedure.

Enantioselective synthesis of amines via reductive amination with a dehydrogenase mutant from Exigobacterium sibiricum: Substrate scope, co-solvent tolerance and biocatalyst immobilization

In recent years, the reductive amination of ketones in the presence of amine dehydrogenases emerged as an attractive synthetic strategy for the enantioselective preparation of amines starting from ketones, an ammonia source, a reducing reagent and a cofactor, which is recycled in situ by means of a second enzyme. Current challenges in this field consists of providing a broad synthetic platform as well as process development including enzyme immobilization. In this contribution these issues are addressed. Utilizing the amine dehydrogenase EsLeuDH-DM as a mutant of the leucine dehydrogenase from Exigobacterium sibiricum, a range of aryl-substituted ketones were tested as substrates revealing a broad substrate tolerance. Kinetics as well as inhibition effects were also studied and the suitability of this method for synthetic purpose was demonstrated with acetophenone as a model substrate. Even at an elevated substrate concentration of 50 mM, excellent conversion was achieved. In addition, the impact of water-miscible co-solvents was examined, and good activities were found when using DMSO of up to 30% (v/v). Furthermore, a successful immobilization of the EsLeuDH-DM was demonstrated utilizing a hydrophobic support and a support for covalent binding, respectively, as a carrier.

Β-phenylalanine ester synthesis from stable β-keto ester substrate using engineered ω-transaminases

The successful synthesis of chiral amines from ketones using ω-transaminases has been shown in many cases in the last two decades. In contrast, the amination of β-keto acids is a special and relatively new challenge, as they decompose easily in aqueous solution. To avoid this, transamination of the more stable β-keto esters would be an interesting alternative. For this reason, ω-transaminases were tested in this study, which enabled the transamination of the β-keto ester substrate ethyl benzoylacetate. Therefore, a ω-transaminase library was screened using a coloring o-xylylenediamine assay. The ω-transaminase mutants 3FCR_4M and ATA117 11Rd show great potential for further engineering experiments aiming at the synthesis of chiral (S)- and (R)-β-phenylalanine esters. This alternative approach resulted in the conversion of 32% and 13% for the (S)- and (R)-enantiomer, respectively. Furthermore, the (S)-β-phenylalanine ethyl ester was isolated by performing a semi-preparative synthesis.

BICYCLIC-PYRIMIDINEDIONE COMPOUNDS

The present invention provides novel bicyclic pyrimidinedione compounds that are useful for the treatment of hypertrophic cardiomyopathy (HCM) and conditions associated with left ventricular hypertrophy or diastolic dysfunction. The synthesis and characterization of the compounds is described, as well as methods for treating HCM and other forms of heart disease.

Chiral Lewis Base-Catalyzed, Enantioselective Reduction of Unprotected β-Enamino Esters with Trichlorosilane

Catalytic asymmetric reduction of N-unsubstituted β-enamino esters represents a major challenge for asymmetric catalysis. In this paper, the first organocatalytic system that could be used for the asymmetric hydrosilylation of N-unsubstituted β-enamino esters has been developed. Using N-tert-butylsulfinyl-L-proline-derived amides and L-pipecolinic acid-derived formamides as catalyst, a broad range of β-aryl- and β-alkyl-substituted free β-amino esters could be prepared with high yields and enantioselectivities. The practicality was illustrated by the gram-scale asymmetric synthesis of ethyl (R)-3-amino-3-phenylpropanoate and isopropyl (S)-3-amino-4-(2,3,5-trifluorophenyl)butanoate. The resulting product can be smoothly transformed to the FDA approved medicines dapoxetine and sitagliptin in a short synthetic route.

Asymmetric synthesis of 2-substituted cyclic amines

Cyanomethylenetributylphosphorane-mediated ring closure for the asymmetric synthesis of 2-substituted cyclic amines such as azetidines, pyrrolidines and a piperidine is reported. The desired stereochemistry at the 2-position was fixed using (S)-tert-butyl sulfinamide as a chiral auxiliary.

Development of a commercial process for (S)-β-phenylalanine (1)

The development of a commercial manufacturing route for (S)-β-phenylalanine 8, a key pharmaceutical building block, is described. The different approaches which were investigated, based on catalytic asymmetric hydrogenation of enamide intermediates and on biocatalysis using acylase and lipase hydrolyses, are compared. The lipase resolution route was chosen for scale-up, and the final two-step process, based on readily available raw materials, is shown to be robust at full manufacturing scale

Chiral lewis base catalyzed highly enantioselective reduction of N-alkyl β-enamino esters with trichlorosilane and water

First, test the water! In the presence of a chiral Lewis base catalyst 2, the supposedly moisture-unfriendly reduction system with trichlorosilane was found to be highly efficient and enantioselective when using water as an additive. For the first time, this method enables the reduction of a broad range of N-alkyl β-enamino esters 1 to give N-alkyl β-amino esters 3 in good to high yields and with excellent enantioselectivities (see scheme).

An efficient new enzymatic method for the preparation of β-aryl-β-amino acid enantiomers

An efficient synthesis of β-aryl-β-amino acid enantiomers has been developed via the lipase-catalysed enantioselective hydrolysis of the corresponding racemic ethyl esters in an organic solvent. High enantioselectivities (E >100) were observed when the lipase PS-catalysed reactions were performed with H2O (0.5 equiv) in diisopropyl ether at 45 °C. The products could be easily separated and were obtained in good yields of ≥40%.