138751-03-8

Basic information

• Product Name: (2R)-2-amino-2-(2-fluorophenyl)acetic acid
• Synonyms: (R)-2-AMINO-2-(2-FLUOROPHENYL)ACETIC ACID; (2R)-amino(2-fluorophenyl)ethanoic acid; (R)-AMINO-(2-FLUORO-PHENYL)-ACETIC ACID
• CAS NO: 138751-03-8
• Molecular Formula: C₈H₈FNO₂
• Molecular Weight: 169.15300
• Mol File: 138751-03-8.mol
• Article Data: 6

Chemical Properties

• CAS DataBase Reference: (2R)-2-amino-2-(2-fluorophenyl)acetic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (2R)-2-amino-2-(2-fluorophenyl)acetic acid(138751-03-8)
• EPA Substance Registry System: (2R)-2-amino-2-(2-fluorophenyl)acetic acid(138751-03-8)

Safety Data

• Hazardous Substances Data: 138751-03-8(Hazardous Substances Data)

Usage

Description

(2R)-2-amino-2-(2-fluorophenyl)acetic acid is a chiral compound with the molecular formula C8H8FNO2. It is a derivative of the amino acid glycine, featuring a fluorine atom attached to the phenyl ring. As a chiral compound, it exists in two enantiomeric forms, (R)and (S)-, with the (2R)-enantiomer possessing unique chemical properties and potential pharmacological effects. This versatile compound is commonly used in the synthesis of pharmaceuticals and as a building block in organic chemistry.

Uses

Used in Pharmaceutical Industry:
(2R)-2-amino-2-(2-fluorophenyl)acetic acid is used as a key intermediate in the synthesis of various pharmaceuticals for its potential to contribute to the development of new drugs. Its unique chemical properties and potential biological activity make it a valuable target for research and drug discovery.
Used in Organic Chemistry:
In the field of organic chemistry, (2R)-2-amino-2-(2-fluorophenyl)acetic acid serves as a building block for the creation of more complex organic molecules. Its structural features allow for further functionalization and modification, facilitating the synthesis of a wide range of organic compounds.
Used in Drug Development:
(2R)-2-amino-2-(2-fluorophenyl)acetic acid is utilized in drug development due to its potential biological activity. Researchers explore its interactions with biological targets to develop new therapeutic agents, particularly in the context of its unique (2R)-enantiomer form, which may offer specific pharmacological effects.

Upstream product

• 446-52-6 2-Fluorobenzaldehyde 
• 389-31-1 2-fluoromandelic acid 
• 394-46-7 2-fluorostyrene 
• 153327-92-5 (+/-)-N-phenylacetyl-o-fluorophenylglycine 
• 84145-28-8 (+/-)-2-amino-2'-fluorophenylacetic acid 
• 153381-38-5 (-)-N-phenylacetyl-o-fluorophenylglycine 
• 153327-93-6 N-Acetyl-α-(2-fluorophenyl)glycine 
• 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 
• 271583-21-2 benzylamino-(2-fluoro-phenyl)-acetic acid 

Relevant articles and documents

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.

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.).

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.