2343-27-3

Usage

Uses

Used in Pharmaceutical Synthesis:
(2-FLUOROPHENYL)GLYCINE is used as a building block for the creation of various pharmaceuticals, leveraging its unique structure to contribute to the development of new drugs.
Used in Agrochemical Synthesis:
In the agrochemical industry, (2-FLUOROPHENYL)GLYCINE serves as a key component in the synthesis of compounds designed to protect crops and enhance agricultural productivity.
Used as an Enzyme Inhibitor:
(2-FLUOROPHENYL)GLYCINE is utilized as an inhibitor of certain enzymes, playing a role in the regulation of biological processes and potentially contributing to therapeutic effects.
Used as a Chiral Auxiliary in Asymmetric Synthesis:
(2-FLUOROPHENYL)GLYCINE is employed as a chiral auxiliary in asymmetric synthesis, aiding in the production of enantiomerically pure compounds, which is crucial for the development of effective and selective pharmaceuticals.

InChI:InChI=1/C8H8FNO2/c9-6-3-1-2-4-7(6)10-5-8(11)12/h1-4,10H,5H2,(H,11,12)

Upstream product

• 271583-21-2 benzylamino-(2-fluoro-phenyl)-acetic acid 
• 153381-38-5 (-)-N-phenylacetyl-o-fluorophenylglycine 
• 394-46-7 2-fluorostyrene 
• 389-31-1 2-fluoromandelic acid 
• 153327-92-5 (+/-)-N-phenylacetyl-o-fluorophenylglycine 
• 84145-28-8 (+/-)-2-amino-2'-fluorophenylacetic acid 
• 573701-88-9 methyl (±)-2-amino-2-(2-fluorophenyl)acetate 
• 79477-86-4 2-fluorophenylglyoxylic acid 
• 133721-88-7 (+/-)-2-hydroxy-2-(2-fluorophenyl)acetonitrile 
• 271583-35-8 2-benzylamino-2-(2-fluoro-phenyl)-acetamide 
• 271583-57-4 Benzylamino-(2-fluoro-phenyl)-acetonitrile 
• 446-52-6 2-Fluorobenzaldehyde 
• 153327-93-6 N-Acetyl-α-(2-fluorophenyl)glycine 

Relevant academic research and scientific papers

Synthesis of Unprotected 2-Arylglycines by Transamination of Arylglyoxylic Acids with 2-(2-Chlorophenyl)glycine

The transamination of α-keto acids with 2-phenylglycine is an effective methodology for directly synthesizing unprotected α-amino acids. However, the synthesis of 2-arylglycines by transamination is problematic because the corresponding products, 2-arylglycines, transaminate the starting arylglyoxylic acids. Herein, we demonstrate the use of commercially available l-2-(2-chlorophenyl)glycine as the nitrogen source in the transamination of arylglyoxylic acids, producing the corresponding 2-arylglycines without interference from the undesired self-transamination process.

Method for continuously and quickly preparing DL-phenylglycine and analogue thereof

The invention provides a method for continuously and quickly preparing DL-phenylglycine and an analogue thereof. The method comprises the steps of adding 2-hydroxyl-phenylacetonitrile and an analoguethereof (cyanohydrin for short) and an aqueous ammonium bicarbonate solution into a microchannel reactor for a reaction, controlling the reaction temperature to be 80-130 DEG C, and controlling the reaction pressure to be 0.5-2.0 MPa, wherein the standing time of the reactants in a microchannel is 1-8 min, and an aqueous solution of 5-phenyl-hydantoin and an analogue thereof (hydantoin for short)is obtained; adding the hydantoin and alkali into the microchannel reactor for a reaction, controlling the reaction temperature to be 120-200 DEG C, and controlling the reaction pressure to be 1.0-3.5MPa, wherein the standing time of the reactants in the microchannel is 1-8 min, and then a saline solution of phenylglycine and an analogue thereof is obtained; conducting acidification neutralization and crystallization to obtain the phenylglycine and the analogue thereof. According to the method, the microchannel reactor is adopted, the reaction time is greatly shorted, the reaction speed is increased, pyrolysis and polymerization of the cyanohydrin are reduced, no by-products are generated, the products are high in yield, clean and environmentally friendly, and the production cost is lowered.

One-Pot Enantioselective Synthesis of d-Phenylglycines from Racemic Mandelic Acids, Styrenes, or Biobased l-Phenylalanine via Cascade Biocatalysis

Enantiopure d-phenylglycine and its derivatives are an important group of chiral amino acids with broad applications in thepharmaceutical industry. However, the existing synthetic methods for d-phenylglycine mainly rely on toxic cyanide chemistry and multistep processes. To provide green and safe alternatives, we envisaged cascade biocatalysis for the one-pot synthesis of d-phenylglycine from racemic mandelic acid, styrene, and biobased l-phenylalanine, respectively. Recombinant Escherichia coli (LZ110) was engineered to coexpress four enzymes to catalyze a 3-step reaction in one pot, transforming mandelic acid (210 mM) to give enantiopure d-phenylglycine in 29.5 g L?1 (195 mM) with 93% conversion. Using the same whole-cell catalyst, twelve other d-phenylglycine derivatives were also produced from the corresponding mandelic acid derivatives in high conversion (58–94%) and very high ee (93–99%). E. coli (LZ116) expressing seven enzymes was constructed for the transformation of styrene to enantiopure d-phenylglycine in 80% conversion via a one-pot 6-step cascade biotransformation. Twelve substituted d-phenylglycines were also produced from the corresponding styrene derivatives in high conversion (45–90%) and very high ee (92–99%) via the same cascade reactions. A nine-enzymeexpressing E. coli (LZ143) was engineered to transform biobased l-phenylalanine to enantiopure d-phenylglycine in 83% conversion via a one-pot 8-step transformation. Preparative biotransformations were also demonstrated. The high-yielding synthetic methods use cheap and green reagents (ammonia, glucose, and/or oxygen), and E. coli whole-cell catalysts, thus providing green and useful alternative methods for manufacturing d-phenylglycine. (Figure presented.).

Highly enantioselective titanium-catalyzed cyanation of imines at room temperature

(Figure presented) A highly active and enantioselective titanium-catalyzed cyanatlon of imines at room temperature Is described. The catalyst used Is a partially hydrolyzed titanium alkoxide (PHTA) precatalyst together with a readily available N-salicyl-β-aminoalcohol ligand. Up to 98% ee was obtained with quantitative yields In 15 min of reaction time using 5 mol % of the catalyst. Various N-protecting groups such as benzyl, benzhydryl, Boc, and PMP are tolerated.

A facile synthesis of substituted phenylglycines

A convenient scaleable process for the preparation of substituted phenylglycines 2 by a modified Strecker reaction is described. Bisulfite- mediated addition of benzylamine and cyanide anion to substituted benzaldehydes 3 gave the aminonitriles 4 which were hydrolysed in two steps to the N-protected amino acid 1. Debenzylation using catalytic transfer hydrogenation gave the title compounds in good yield.

HOMOCHIRAL HETEROORGANIC ANALOGS OF NATURAL COMPOUNDS. I. PREPARATIVE BIOCATALYTIC METHOD OF OBTAINING FLUORINE-CONTAINING L- AND D-PHENYLGLYCINES

A biocatalytic method of obtaining homochiral o- and p-fluorine-substituted phenylglycines by enantiomeric hydrolysis from N-phenylacetyl or N-acetyl derivatives under the action of Escherichia coli penicillin acylase or Streptoverticillium olivoreticuli aminoacylase is proposed.The L form of the amino acid and the unhydrolyzed D-enantiomer of the initial derivative are separated by extraction and chromatographic methods.The acid hydrolysis of the D-enantiomers of N-phenylacetyl derivatives of fluorine-substituted phenylglycines leads to partial (about 15percent) racemization.With a substantially higher (by two orders of magnitude) concentration of enzyme and an increase in the reaction time it is possible to use penicillinase as a catalyst for the hydrolysis of the D-enantiomer of the N-phenylacetyl derivative not accompanied by any appreciable racemization whatever.