164453-67-2

Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-AMINO-3-O-TOLYL-PROPIONIC ACID ETHYL ESTER is used as a chiral building block for the synthesis of various biologically active compounds. Its application is primarily due to its ability to contribute to the creation of pharmaceuticals and agrochemicals with specific stereochemistry, which is crucial for their efficacy and safety.
Used in Organic Synthesis:
In the field of organic synthesis, (S)-2-AMINO-3-O-TOLYL-PROPIONIC ACID ETHYL ESTER serves as an essential intermediate. It is used for the production of chiral drugs, where its unique structural properties allow for the creation of molecules with specific configurations that are vital for their intended biological functions.
Used in the Synthesis of Biologically Active Compounds:
(S)-2-AMINO-3-O-TOLYL-PROPIONIC ACID ETHYL ESTER is also employed in the synthesis of biologically active compounds, which have potential applications in various therapeutic areas. Its role in this context is to provide the necessary chiral framework for the development of these compounds, ensuring their effectiveness and selectivity in targeting specific biological processes.

Upstream product

• 100-39-0 benzyl bromide 
• 617-35-6 2-oxo-propionic acid ethyl ester 
• 1115954-61-4 ethyl (S)-2-azido-2-methyl-3-phenylpropanoate 
• 134279-44-0 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'-benzyloxycarbonylamino-2'-methyl-3'-phenylpropanoate 
• 123463-91-2 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen benzylmalonate 
• 123463-78-5 (1R,3R,4S)-8-phenyl-p-menthan-3-yl hydrogen benzyl(methyl)malonate 
• 157718-85-9 (2S)-2-[(methoxycarbonyl)amino]-2-methyl-3-phenylpropanonitrile 
• 46438-07-7 α-methyl-α-carbethoxy-β-phenethylamine 
• 64-17-5 ethanol 
• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 

Downstream Products

• 23239-35-2 (S)-2-amino-2-methyl-3-phenylpropanoic acid 
• 123618-23-5 ethyl (2S)-2-acetylamino-2-methyl-3-phenylpropanoate 

Relevant academic research and scientific papers

High-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid

The invention discloses a high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid. The high-chirality method for selectively synthesizing alpha-disubstituted alpha-amino acid is characterized by comprising the following steps: step one, reacting S-tert-butanesulfinyl amide or R-tert-butanesulfinyl amide, R-beta substituted ethyl pyruvate and tetraethyl titanate in atetrahydrofuran solvent to obtain a compound C; step two, reacting the compound C with alkyl substituted magnesium bromide under the catalyzing effect of zinc dimethyl in tetrahydrofuran to obtain acompound E; step three, reacting the compound E under the effect of ammonium chloride and anhydrous hydrogen chloride to obtain a compound F; and step four, hydrolyzing the compound F in an ethanol aqueous solution of sodium hydroxide to obtain hydrochloride of a compound G, and carrying out ion exchange to obtain the compound G. The chiral selective reaction is greatly improved, and the method issimple in process, uses cheap and easily obtained raw materials, is simple and convenient to operate, is quite suitable for industrial mass production, and has quite extensive industrial applicationprospect and market value.

Mitsunobu approach to the synthesis of optically active α,α-disubstituted amino acids

Chiral tertiary α-hydroxy esters of known stereochemical configuration were transformed to α-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the α-carbon. Several α,α- disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

Enantioselective biotransformation of α,α-disubstituted dinitriles to the corresponding 2-cyanoacetamides using Rhodococcus sp. CGMCC 0497

A new application of nitrile-converting enzymes in the synthesis of optically active α,α-disubstituted-α-cyanoacetamides from α,α-disubstituted-malononitriles with whole cells of Rhodococcus sp. CGMCC 0497 is described. The products were obtained with enantiomeric excesses of up to >99%, and yields of up to 53%. They are very useful chiral intermediates especially for the synthesis of chiral α,α-disubstituted amino acids but have never been synthesized directly by chemical or enzymatic methods.

Chemo-Enzymic Synthesis of Optically Active α,α-Disubstituted α-Amino Acids

A series of α,α-disubstituted α-amino esters was chemically synthesized and then resolved through enantioselective hydrolysis catalysed by a new enzyme isolated from crude Humicola langinosa lipase.This enzyme only accepts free amino esters as substrates with neither lipase activity toward olive oil nor esterase activity toward o-nitrophenyl butyrate.It is unique in that it successfully catalyses the resolution of amino esters with two large α-alkyl groups including aliphatic, aromatic and cyclic amino esters.Examples of resolutions where the alkyl groups differ in size by as little as a single carbon atom have been demonstrated.For determination of absolute configuration, some of the optically active α,α-disubstituted amino acids were also prepared through Schoellkopf's asymmetric synthesis and the structures were verified by X-ray crystallography.A model depicting the substrate binding site of the enzyme is proposed.

Synthesis, resolution and absolute configuration determination of (S)- and (R)-4-formyl-5-hydroxyparacyclophane and its application in the asymmetric synthesis of α-amino acids

Racemic (R,S)-4-formyl-5-hydroxyparacyclophane (FHPC) was resolved into enantiomers via its Schiff's base with (S)- and (R)-α-phenylethylamine (α-PEAM) and its absolute configuration was determined by an X-ray diffraction structural study.Scalemic FHPC or its derivatives can be used as chiral auxiliaries for the asymmetric synthesis of β-hydroxy-α-amino acids and α-methylphenylalanine with ees ranging mostly from 45 to 98percent.

Stereoselective Alkylation of Dianions derived from Chiral Half-Esters of Monosubstituted Malonic Acids: Asymmetric Synthesis of α-Alkyl α-Amino Acids and Key Synthetic Intermediates for Hunteria and Aspidosperma Indole Alkaloids

Substitution of the chiral half-esters of monosubstituted malonic acids with halides leads to the formations of mixtures of the diastereomeric alkyl- or benzyl-malonic half-esters.The (R)-isomers (13A and 15A-22A) were obtained from the phenylmenthyl half-ester 14 of methylmalonic acid in high diastereoisomeric excess.The same stereoisomers were also produced by reaction of the half-esters 9, 23 and 24 with methyl iodide.Their absolute configurations were determined by transforming the major products into the known α-alkyl α-amino acid derivatives 30, 33 and 35.The major product 43, prepared by allylation of the half-ester 9, was converted into two lactones 41 and 42, key intermediates for synthesis of indole alkaloids of the Hunteria and Aspidosperma types.The mechanism of the above alkylation is discussed.