29738-09-8

Usage

Uses

Used in Pharmaceutical Industry:
Benzeneacetic acid, alpha-amino-alpha-methyl-, (alphaR)(9CI) is used as a precursor in the synthesis of various pharmaceutical compounds for its ability to facilitate the production of complex organic molecules with specific chiral configurations. Its role in the synthesis process is crucial for the development of effective and targeted drug therapies.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
In the field of organic chemistry, Benzeneacetic acid, alpha-amino-alpha-methyl-, (alphaR)(9CI) is utilized as a chiral auxiliary to control the stereochemistry of asymmetric synthesis reactions. Its unique chiral center allows for the selective formation of desired enantiomers, which is essential for the production of biologically active compounds with specific pharmacological properties.
Used in the Preparation of Amine Derivatives:
Benzeneacetic acid, alpha-amino-alpha-methyl-, (alphaR)(9CI) serves as a reagent in the preparation of amine derivatives, which are important building blocks in the synthesis of various organic compounds and pharmaceuticals. Its ability to react with other chemical entities enables the formation of a wide range of amine-containing molecules with diverse applications.
Used in Research and Development of Drug Compounds:
Due to its potential pharmacological properties, Benzeneacetic acid, alpha-amino-alpha-methyl-, (alphaR)(9CI) is employed in the research and development of novel drug compounds. Its involvement in this process aids in the discovery and optimization of new therapeutic agents with improved efficacy and selectivity.

Upstream product

• 360566-30-9 (R)-2-Amino-2-phenyl-propionic acid methyl ester 
• 201607-11-6 (R)-3-methyl-5-methyl-5-phenylimidazolidine-2,4-dione 
• 67-56-1 methanol 
• 4285-42-1 N-phenyl-N-methylcarbamoyl chloride 
• 201607-11-6 (R)-3,5-dimethyl-5-phenylimidazolidine-2,4-dione 
• 73872-14-7 (2S,4'S,5'S)-(+)-2-Amino-N-(2',2'-dimethyl-4'-phenyl-1',3'-dioxan-5'-yl)-2-phenylacetonitril 
• 100-52-7 benzaldehyde 
• 4355-46-8 α-amino-α-methylphenylacetonitrile 
• 82944-84-1 N-[(1E)-1-phenylethylidene]-P,P-diphenylphosphinic amide 
• 613-91-2 acetophenone oxime 
• 98-86-2 acetophenone 
• 1115955-05-9 benzyl (R)-2-azido-2-phenylpropanoate 
• 19196-63-5 DL-α-methylphenylglycine amide 
• 185396-31-0 (-)-N-benzoyl-α-hydroxymethylphenylglycine 

Downstream Products

• 746637-52-5 (R)-N²-<(benzyloxy)carbonyl>-2-methyl-2-phenylglycine 
• 191422-05-6 (S)-3-Benzyloxycarbonylamino-N-((R)-1-methoxycarbonyl-1-phenyl-ethyl)-succinamic acid tert-butyl ester 
• 191422-06-7 (S)-3-Benzyloxycarbonylamino-N-((R)-1-methoxycarbonyl-1-phenyl-ethyl)-succinamic acid 
• 711015-17-7 Cbz-D-(α-Me)Phg-NH-t-Bu 
• 746637-65-0 C₃₄H₃₂N₂O₇ 
• 746637-72-9 [(R)-1-((R)-1-Carbamoyl-1-phenyl-ethylcarbamoyl)-1-phenyl-ethyl]-carbamic acid benzyl ester 
• 746637-54-7 2-benzyloxy-4-methyl-4-phenyl-4H-oxazol-5-one 
• 515-30-0 2-phenyllactic acid 
• 360566-30-9 (R)-2-Amino-2-phenyl-propionic acid methyl ester 
• 1117977-29-3 C₂₄H₁₉Cl₄NO₅ 

Relevant academic research and scientific papers

α-Methyl phenylglycines by asymmetric α-arylation of alanine and their effect on the conformational preference of helical Aib foldamers

α-Arylated alanine derivatives were made enantioselectively by migratory rearrangement of a urea derivative using (R,R)-pseudoephedrine as a chiral auxiliary. Incorporation of a single residue of the product α-methyl phenylglycine into an otherwise achiral oligomer of aminoisobutyric acid oligomer induced a preferred screw sense, detectable by a NMR reporter located at the remote terminus of the oligomer. The magnitude of the screw sense induction was greater when the chiral residue was located at the N-terminus of the foldamer, and in some cases the sense of induction was opposite to that of related α-methylated amino acids with α-substituents other than aryl.

Enantioselective Synthesis of α-Quaternary Amino Acids by Alkylation of Deprotonated α-Aminonitriles

A series of α-quaternary arylglycines were prepared in high optical purity (up to 98% ee) by α-alkylation of deprotonated α-aminonitriles derived by the Strecker reaction from (4S,5S)-5-amino-2,2-dimethyl-4-phenyl-1,3-dioxane. The procedure includes only chromatographic purification of the final products and is devoid of chromatography or crystallization operations on intermediates to raise the optical purity.

Pseudoephedrine-Directed Asymmetric α-Arylation of α-Amino Acid Derivatives

Available α-amino acids undergo arylation at their α position in an enantioselective manner on treatment with base of N′-aryl urea derivatives ligated to pseudoephedrine as a chiral auxiliary. In situ silylation and enolization induces diastereoselective migration of the N′-aryl group to the α position of the amino acid, followed by ring closure to a hydantoin with concomitant explulsion of the recyclable auxiliary. The hydrolysis of the hydantoin products provides derivatives of quaternary amino acids. The arylation avoids the use of heavy-metal additives, and is successful with a range of amino acids and with aryl rings of varying electronic character.

Nitrilases, nucleic acids encoding them and methods for making and using them

The invention relates to nitrilases and to nucleic acids encoding the nitrilases. In addition methods of designing new nitrilases and method of use thereof are also provided. The nitrilases have increased activity and stability at increased pH and temperature.

Bifunctional iminophosphorane organocatalysts for enantioselective synthesis: Application to the ketimine nitro-Mannich reaction

The design, synthesis, and development of a new class of modular, strongly basic, and tunable bifunctional Bronsted base/H-bond-donor organocatalysts are reported. These catalysts incorporate a triaryliminophosphorane as the Bronsted basic moiety and are readily synthesized via a last step Staudinger reaction of a chiral organoazide and a triarylphosphine. Their application to the first general enantioselective organocatalytic nitro-Mannich reaction of nitromethane to unactivated ketone-derived imines allows the enantioselective construction of β-nitroamines possessing a fully substituted carbon atom. The reaction is amenable to multigram scale-up, and the products are useful for the synthesis of enantiopure 1,2-diamine and α-amino acid derivatives.

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.

The proline-catalyzed asymmetric amination of branched aldehydes

An efficient access to configurationally stable α,β- disubstituted α-amino aldehydes, oxazolidinones, and α-amino acids has been presented. Starting from simple and easily available racemic aldehydes, the α-aminated products were obtained using azodicarboxylates as the nitrogen source in up to 86 % ee and moderate to excellent yield. These products could further be converted both into the corresponding α-amino alcohols and, depending on the residue of the azodicarboxylates and the reaction conditions, into the oxazolidinones. On the other hand, oxidation towards the carboxylic acid and cleavage of the hydrazide bond under mild conditions revealed the free α-alkylated phenylglycine derivative. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.

Synthesis of optically active α-methylamino acids and amides through biocatalytic kinetic resolution of amides

Catalyzed by Rhodococcus sp. AJ270, a nitrile hydratase and amidase containing microbial whole-cell catalyst, under very mild conditions, a number of racemic α-methylamino amides were resolved into the corresponding optically active (S)-(+)-α-methylamino acids and (R)-(-)-α- methylamino amides. The steric requirement of the amidase against α-amino phenylacetamides bearing methyl group(s) at α-amino nitrogen and/or α-carbon was also studied. Coupled with the chemical hydrolysis of amide, the biotransformation process provided a direct synthesis of α-methylamino acids in both enantiomeric forms from readily available racemic amides.

Efficient biocatalytic synthesis of highly enantiopure α-alkylated arylglycines and amides

A number of racemic α-alkylarylglycine amides including 1-amino-1-carbamoyl-1,2,3,4-tetrahydronaphthalene underwent efficient biocatalytic hydrolysis under very mild conditions to afford the corresponding (S)-α-alkylarylglycines and (R)-α-alkylarylglycine