24593-48-4

Usage

Uses

Used in Pharmaceutical Industry:
L-4-Methoxyphenylglycine is used as a chiral building block for the synthesis of various drugs, including anti-inflammatory and anti-cancer medications. Its unique structure and properties make it a valuable compound in the development of new pharmaceuticals.
Used in Agrochemical Industry:
L-4-Methoxyphenylglycine is also used as an intermediate in the synthesis of agrochemicals, contributing to the development of effective and targeted pesticides and other agricultural products.
Used in Organic Synthesis:
L-4-Methoxyphenylglycine is employed in organic synthesis for the preparation of complex molecules, showcasing its versatility and importance in the field of chemistry. Its unique properties allow for the creation of a wide range of compounds with various applications.

Upstream product

• 42456-26-8 2-amino-2-(4-methoxyphenyl)acetonitrile 
• 2540-53-6 2-(4-methoxyphenyl)glycine 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 145057-96-1 (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-methoxyphenyl)ethanoic acid 
• 139224-89-8 (R)-2-<(2-hydroxy-1-phenylethyl)amino>-2-(4-methoxyphenyl)ethanenitrile 
• 145058-04-4 methyl (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-methoxyphenyl)ethanoate 
• 129505-11-9 (2S,2'S)-N-<2'-(hydroxyamino)-2'-(4''-methoxyphenyl)acetyl>bornane-10,2-sultam 
• 129505-04-0 (2S)-N-<(4-methoxyphenyl)acetyl>bornane-10,2-sultam 
• 139224-89-8 N-<(R)-2-hydroxy-1-phenylethyl>-(S)-α-amino-4-methoxybenzeneacetonitrile 
• 123-11-5 4-methoxy-benzaldehyde 
• 85803-46-9 (R)-N-(p-Methoxybenzylidene)-2-amino-2-phenylethanol 
• 76986-15-7 2-amino-2-(4-methoxyphenyl)acetamide 
• 1037074-17-1 (S)-(4-Methoxy-phenyl)-{[1-phenyl-meth-(Z)-ylidene]-amino}-acetonitrile 
• 52771-14-9 2-acetamido-2-(4-methoxyphenyl) acetic acid 

Downstream Products

• 32462-30-9 (S)-hydroxyphenylglycine 
• 191109-48-5 (S)-2-amino-2-(4-methoxyphenyl)-1-ethanol 
• 169273-94-3 (S)-(N-benzyloxycarbonyl)-p-methoxyphenylglycine 

Relevant academic research and scientific papers

Large α-aminonitrilase activity screening of nitrilase superfamily members: Access to conversion and enantiospecificity by LC-MS

A high-throughput screening for the identification of nitrilases demonstrating activity towards alpha-aminonitriles is reported. A LC-MS assay giving access to both conversion and enantiospecificity was developed. 588 candidate enzymes were screened as cell lysates against six alpha-aminonitriles in 96-well microplates. The candidate enzymes were selected following two criteria, their sequence identity with a set of known nitrilases or their phylogenetic position among the nitrilase superfamily. Five enzymes were identified and found to hydrolyse alpha-aminonitrile into the corresponding alpha-aminoacid. The substrate range was found to be very narrow as only two different alpha-aminonitriles, 2-aminovaleronitrile and 2-amino-2- phenylacetonitrile, were found to be substrates. The biocatalytic capabilities of three enzymes were further investigated and the best result was obtained with an enzyme from Burkholderia xenovorans catalysing the enantiospecific hydrolysis of 2-aminovaleronitrile into (S)-norvaline with excellent conversion and enantiomeric excess.

Practical and convenient enzymatic synthesis of enantiopure α-amino acids and amides

Catalyzed by the nitrile hydratase and the amidease in Rhodococcus sp. AJ270 cells under very mild conditions, a number of α-aryl- and α-alkyl-substituted DL-glycine nitriles 1 rapidly underwent a highly enantioselective hydrolysis to afford D-(-)-α-amino acid amides 2 and L-(+)-α-amino acids 3 in high yields with excellent enantiomeric excesses in most cases. The overall enantioselectivity of the biotransformations of nitriles originated from the combined effects of a high L-enantioselective amidase and a low enantioselective nitrile hydratase. The influence of the substrates on both reaction efficiency and enantioselectivity was also discussed in terms of steric and electronic effects. Coupled with chemical hydrolysis of D-(-)-α-phenylglycine amide, biotransformation of DL-phenylglycine nitrile was applied in practical scale to produce both D- and L-phenylglycines in high optical purity.

Highly efficient and enantioselective synthesis of L-arylglycines and D-arylglycine amides from biotransformations of nitriles

Under very mild conditions, the Rhodococcus sp. AJ270-catalysed biotransformation of arylglycine nitriles 1, prepared easily from the reaction of substituted benzaldehydes, ammonium chloride and potassium cyanide, proceeded efficiently to produce optically active D-arylglycine amides 2 and L-arylglycines 3 in excellent yields with enantiomeric excesses higher than 99%.

A simple and efficient diastereoselective Strecker synthesis of optically pure α-arylglycines

A simple and economical method for the synthesis of highly functionalised α-amino nitriles, precursors to α-arylglycines with high optical purity is reported. For this purpose, (R) or (S)-2-amino-2- phenylethanol were used as chiral auxiliaries in a 1,3 Strecker reaction. Reactions were studied with a broad range of reagent systems for the generation of cyano nucleophile. Methodology has been extended for the synthesis of (S)-α-(2-iodo-5-nitrophenyl)glycine, (S)-α-(4- methoxyphenyl)glycine and (R)-β-(4-methoxyphenyl)alanine.

Syntheses of optically active α-amino nitrites by asymmetric transformation of the second kind using a principle of O. Dimroth

A mixture of solids As and Bs in equilibrium with the dissolved compounds A1 and B1 is transformed completely into one pure solid, say Bs, if the dissolved compounds A1?B1 are equilibrating in solution. This is applied to transform 1:1 mixtures of solid diastereomeric amygdalates (2-hydroxy-2-phenylacetates; mandelates) (R,R)-3 + (S,R)-3 prepared from racemic α-amino nitriles (R,S)-1 with (R)-mandelic acid 2 into stereochemically pure single diastereomers (R,R)-3, or (S,R)-3 (de > 97%) ('asymmetric transformation of the second kind by application of Dimroth's principle'). Decomposition of the amygdalates (R,R)-3, or (S,R)-3, with aqueous base affords the enantiomerically pure α-amino nitriles (A)-1, or (S)-1 (ten examples). The chiral auxiliary (R)-mandelic acid is recovered almost quantitatively. The optically active α-amino nitriles are hydrolyzed to amides 6, and further to α-N-alkylamino acids 7. N-Benzylamino acids 7 are hydrogenated to α-amino acids 8. Some of the optically active α-amino nitriles 1 are reduced to optically active 1,2-diamines 9. In most cases, absolute configurations could be assigned by comparison of the specific rotations observed with those of authentic compounds.

Efficient chemoenzymatic synthesis of enantiomerically pure α-amino acids

A general two-step chemoenzymatic synthesis for enantiomerically pure natural and nonnatural α-amino acids is presented. In the first step of the sequence, the ubiquitous educts aldehyde, amide and carbon monoxide react by palladium-catalyzed amidocarbonylation to afford the racemic N-acyl amino acids in excellent yields. In the second step, enzymatic enantioselective hydrolysis yields the free optically pure a-amino acid and the other enantiomer as the N-acyl derivative, both in optical purities of 85-99.5% ee. The advantage of the chemoenzymatic process compared to other amino acid synthesis are demonstrated by the preparation of various functionalized (-OR, -Cl, -F, -SR) α-amino acids on a 10-g scale.

The reaction between C- and/or N-terminal protected α-aminoacid and sodium hydrogen telluride

Sodium hydrogen telluride selectively removed C-terminal alkyl group of C- and/or N-terminal protected α-aminoacids with yields ranging from 70% to 95%.

Asymmetric Synthesis of α-Amino Acids and α-N-Hydroxyamino Acids from N-Acylbornane-10,2-sultams: 1-Chloro-1-nitrosocyclohexane as a Practical +> Equivalent

Successive treatment of N-acylsultams 3 with sodium hexamethyldisilazide, 1-chloro-1-nitrosocyclohexane (1), and aq.HCl gave diastereoisomerically pure, crystalline N-hydroxyamino-acid derivatives 5.These were converted into various amino acids 7, N-hydroxyamino acids 8, and an N-Boc-amino acid 9. (S,S)-Isoleucine (17) and (S,S)-2-acetamido-3-phenylbutyric acid (23) were obtained from N-crotonoylsultam 15 via 1,4-addition of an organomagnesium or organocopper reagent followed by enolate 'amination' with 1.

Synthesis of Optically Active Arylglycines by Photolysis of Optically Active (β-Hydroxyamino) Carbene-Chromium(0) Complexes

Photolysis of chromium complexes having the optically active amino alcohol (1R,2S)-(-)- or (1S,2R)-(+)-2-amino-1,2-diphenylethanol as the amino group produced aryl-substituted oxazinones in good yield with reasonable diastereoselectivity.Facile separation of diastereoisomers followed by mild reductive cleavage produced several arylglycines, having either electron-donating or withdrawing groups on the aromatic ring, in good overall yield and with excellent enantiomeric excess.

An Efficient and Practical Synthesis of L-α-Amino Acids Using (R)-Phenylglycinol as a Chiral Auxiliary

L-α-Amino acids including L-α-arylglycines were conveniently and stereoselectively synthesized via the α-amino carbonitriles given by the Strecker reaction of (R)-2-amino-2-phenylethanol with aldehydes and hydrogen cyanide.The stereoselectivity of these α-amino carbonitriles was thermodynamically controlled.