23239-35-2

Usage

Chemical Properties

White fine crystalline powder

InChI:InChI=1/C10H13NO2.H2O/c1-7-4-2-3-5-8(7)6-9(11)10(12)13;/h2-5,9H,6,11H2,1H3,(H,12,13);1H2/t9-;/m0./s1

Upstream product

• 117466-13-4 α-methyl phenylalanine amide 
• 46438-07-7 α-methyl-α-carbethoxy-β-phenethylamine 
• 100-39-0 benzyl bromide 
• 302-72-7 rac-Ala-OH 
• 10065-72-2 L-Alanine methyl ester 
• 420-37-1 trimethoxonium tetrafluoroborate 
• 134279-44-0 (1R,3R,4S)-8-phenyl-p-menthan-3-yl (2'S)-2'-benzyloxycarbonylamino-2'-methyl-3'-phenylpropanoate 
• 116562-88-0 (R)-N-acetyl-α-methylphenylalanine ethyl ester 
• 97206-21-8 N-(benzyloxycarbonyl)-α-methyl-D-phenylalanine 
• 98061-18-8 (S)-2-Isocyanato-2-methyl-3-phenyl-propionic acid methyl ester 
• 65484-48-2 (4S)-4-Benzyl-4-methyl-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 
• 121703-95-5 N-Chloroacetyl-α-methylphenylalanine 
• 157718-85-9 (2S)-2-[(methoxycarbonyl)amino]-2-methyl-3-phenylpropanonitrile 
• 126402-81-1 isopropyl 2-[(E)-1-phenylmethylideneamino]propanoate 

Downstream Products

• 28385-45-7 L-α-methylphenylalanine methyl ester 
• 53940-89-9 Boc-L-α-Methylphenylvalin*Dicyclohexylamin 
• 164453-67-2 ethyl (S)-2-amino-2-methyl-3-phenylpropionate 
• 111771-58-5 BOC-D-(αMe)Phe-OH 
• 14715-67-4 Ac-L-(αMe)Phe-OH oxazol-5(4H)-one 
• 113806-16-9 (S)-5-benzyl-5-methylimidazolidine-2,4-dione 
• 97206-19-4 (2S)-2-benzyloxycarbonylamino-2-methyl-3-phenylpropanoic acid 
• 53940-88-8 (S)-2-(((1,1-dimethyl)ethoxycarbonyl)amino)-2-methyl-3-phenylpropanoic acid 
• 35409-82-6 (S)-2-amino-2-methyl-3-phenylpropan-1-ol2-amino-1-methoxypropane 
• 135944-05-7 (2S)-2-[9H-fluorene-9-ylmethoxycarbonylamino]-2-methyl-3-phenylpropanoic acid 
• 192064-93-0 (S)-2-((S)-2-tert-Butoxycarbonylamino-2-methyl-3-phenyl-propionylamino)-3-(1H-imidazol-4-yl)-propionic acid methyl ester 
• 123618-23-5 ethyl (2S)-2-acetylamino-2-methyl-3-phenylpropanoate 
• 1428736-40-6 (2R,5S)-5-benzyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 
• 1428736-42-8 (2S,5S)-5-benzyl-5-methyl-2-(pyridine-2-yl)imidazolidine-4-one 

Relevant academic research and scientific papers

Application of Threonine Aldolases for the Asymmetric Synthesis of α-Quaternary α-Amino Acids

We report the synthesis of diverse β-hydroxy-α,α-dialkyl-α-amino acids with perfect stereoselectivity for the α-quaternary center through the action of l- and d-specific threonine aldolases. A wide variety of aliphatic and aromatic aldehydes were accepted by the enzymes and conversions up to >80 % were obtained. In the case of d-selective threonine aldolase from Pseudomonas sp., generally higher diastereoselectivities were observed. The applicability of the protocol was demonstrated by performing enzymatic reactions on preparative scale. Using the d-threonine aldolase from Pseudomonas sp., (2R,3S)-2-amino-3-(2-fluorophenyl)-3-hydroxy-2-methylpropanoic acid was generated in preparative amounts in one step with a diastereomeric ratio >100 favoring the syn-product. A Birch-type reduction enabled the reductive removal of the β-hydroxy group from (2S)-2-amino-3-hydroxy-2-methyl-3-phenylpropanoic acid to generate enantiopure l-α-methyl-phenylalanine via a two-step chemo-enzymatic transformation.

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.

METHOD FOR PRODUCING AMINO ACID AND AMINO ACID SYNTHESIS KIT

PROBLEM TO BE SOLVED: To provide a method for producing an amino acid and an amino acid synthesis kit, which enable synthesis of a desired amino acid in high stereoselectivity efficiently and in a very short time, irrespective whether a radioactive isotope is contained or not. SOLUTION: A method for producing an amino acid and an amino acid synthesis kit are disclosed. The method for producing an amino acid of the present invention comprises a step of alkylating a substrate compound with an alkylating agent in the presence of an optically active phase transfer catalyst as well as a medium and an inorganic base. An amount of use of the optically active phase transfer catalyst is 1 equivalent or more and 1000 equivalents or less relative to the alkylating agent. According to the present invention, a desired amino acid and a derivative thereof can be produced in high stereoselectivity efficiently and in a very short time. Therefore, the present production method is useful, for example, for research and development, and production of a radioactively labelled amino acid and a derivative thereof, which can be used as a tracer for neurodegenerative diseases such as Parkinson disease and Alzheimer disease, heart diseases, and cancerous diseases. SELECTED DRAWING: None COPYRIGHT: (C)2016,JPOandINPIT

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE a-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL] ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active α-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active α,α-disubstituted α-amino acid, and to provide an intermediate useful for the above production methods of an optically active α-amino acid and an optically active α,α-disubstituted α-amino acid. The present invention provides a production method of an optically active α-amino acid or a salt thereof, the production method comprising introducing a substituent into the α carbon in the α-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure α-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

METHOD FOR SYNTHESIZING OPTICALLY ACTIVE α-AMINO ACID USING CHIRAL METAL COMPLEX COMPRISING AXIALLY CHIRAL N-(2-ACYLARYL)-2-[5,7-DIHYDRO-6H-DIBENZO[c,e]AZEPIN-6-YL]ACETAMIDE COMPOUND AND AMINO ACID

Objects of the present invention are to provide an industrially applicable method for producing an optically active ±-amino acid in high yield and in a highly enantioselective manner, to provide a simple production method of an optically active ±,±-disubstituted ±-amino acid, and to provide an intermediate useful for the above production methods of an optically active ±-amino acid and an optically active ±,±-disubstituted ±-amino acid. The present invention provides a production method of an optically active ±-amino acid or a salt thereof, the production method comprising introducing a substituent into the ± carbon in the ±-amino acid moiety of a metal complex represented by the following Formula (1): by an alkylation reaction, an aldol reaction, the Michael reaction, or the Mannich reaction, and releasing an optically pure ±-amino acid enantiomer or a salt thereof by acid decomposition of the metal complex.

Chiral ligand-exchange resolution of underivatized amino acids on a dynamically modified stationary phase for RP-HPTLC

The synthesis of Spi(τ-dec), derived from the selective alkylation of L-spinacine (4,5,6,7-tetrahydro-1H-imidazo[4,5-c]pyridine-6-carboxylic acid) at the τ-nitrogen of its heteroaromatic ring, with a linear hydrocarbon chain of 10 carbon atoms, is described here for the first time. Spi(τ-dec) was successfully employed in the past to prepare home-made chiral columns for chiral ligand-exchange high-performance liquid chromatography. In the present article a new method is described, using Spi(τ-dec) as a chiral selector in high-performance thin-layer chromatography (HPTLC): commercial hydrophobic plates were first coated with Spi(τ-dec) and then treated with copper sulfate. The performance of this new chiral stationary phase was tested against racemic mixtures of aromatic amino acids, after appropriate optimization of both the conditions of preparation of the plates and the mobile phase composition. The enantioselectivity values obtained for the studied compounds were higher than those reported in the literature for similar systems. The method employed here for the preparation of chiral HPTLC plates proved practical, efficient, and inexpensive. Chirality 26:313-318, 2014. 2014 Wiley Periodicals, Inc.

Enantiocatalytic activity of substituted 5-benzyl-2-(pyridine-2-yl) imidazolidine-4-one ligands

Currently, asymmetric synthesis represents one of the main streams of organic synthesis. Although an extensive research has been carried out in this area, the synthesis of chiral compounds with the required enantiomeric purity is still a challenging issue. Herein, we focus on the preparation of new enantioselective catalysts based on pyridine-imidazolidinones. The substituted 5-benzyl-2-(pyridine-2-yl)imidazolidine-4-ones 5-8 were prepared by condensation of chiral amino acid amides (α-methylDOPA and α- methylphenylalanine) with 2-acetylpyridine and pyridine-2-carbaldehyde. The individual isomers of the described ligands 5-8 were separated chromatographically. The copper(II) complexes of these chiral ligands were studied as enantioselective catalysts for the asymmetric Henry reaction of substituted aldehydes with nitromethane or nitroethane. The ligands containing a methyl group at the 2-position of the imidazolidinone ring 6a and 8a exhibit a high degree of enantioselectivity (up to 91% ee). The nitroaldols derived from nitroethane (2-nitropropan-1-ols) were obtained with a comparable enantiomeric purity to derivatives of 2-nitroethanol. This group of ligands represents a new and promising class of enantioselective catalysts, which deserve further attention.

Synthesis of quaternary α-methyl α-amino acids by asymmetric alkylation of pseudoephenamine alaninamide pivaldimine

The utility of pseudoephenamine as a chiral auxiliary for the alkylative construction of quaternary α-methyl α-amino acids is demonstrated. The method is notable for the high diastereoselectivities of the alkylation reactions, for its versatility with respect to electrophilic substrate partners, and for its mild hydrolysis conditions, which provide α-amino acids without salt contaminants. Alternatively, α-amino esters can be obtained by direct alcoholysis.

Asymmetric synthesis of α-methyl-α-amino acids via diastereoselective alkylation of (1s)-(+)-3-carene derived tricyclic iminolactone

A novel carene-based alanine-equivalent tricyclic iminolactone 16 has been synthesized via stereoselective dihydroxylation of the double bond, IBX oxidation of the secondary alcohol, esterification of the tertiary alcohol, deprotection of the resulting ester, and subsequent cyclization from commercially available (1S)-(+)-3-carene in 79% overall yield. The iminolactone 16 demonstrated high reactivity toward alkylation with a wide range of electrophiles at room temperature under phasetransfer catalysis conditions. The alkylated products were produced with excellent diastereoselectivities (>98% de) in good isolated yields (86-94%). High yields (83-91%) of optically pure (S)-R-methyl-R-substituted-R-amino acids were obtained by basic hydrolysis of the dialkylated iminolactones with the recovery of the chiral auxiliary 15 (78-87%).

(S)-α-methyl,α-amino acids: A new stereocontrolled synthesis

A new and convenient stereocontrolled synthesis of the optically pure (S)-α-methyl,α-amino acids 6(a-d) that exploits the chiral synthon 1,4-N,N-[(S)-1-phenylethyl]-piperazine-2,5-dione (1) is described. The (S)-1-phenylethyl group, bonded to each of the N-atoms of the 2,5-diketopiperazine, acts as a chiral inductor in the first alkylation, while the steric hindrance appears to be the determining factor of stereocontrol in third and forth alkylation.