19883-57-9

Usage

Uses

Used in Pharmaceutical Industry:
(S)-4-Fluorophenylglycine is used as an intermediate for the synthesis of various drugs, particularly in the development of novel pharmaceuticals with improved efficacy and selectivity. Its optically active nature allows for the creation of enantiomerically pure compounds, which is essential for ensuring the desired biological activity and minimizing potential side effects.
As an intermediate, (S)-4-Fluorophenylglycine plays a vital role in the production of drugs targeting a wide range of medical conditions, including but not limited to cardiovascular diseases, neurological disorders, and various types of cancer. Its incorporation into drug molecules can lead to enhanced pharmacokinetic properties, such as improved solubility, bioavailability, and targeted delivery to specific tissues or organs.

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

Upstream product

• 153381-37-4 N-acetyl-4-fluorophenylglycine 
• 7292-73-1 (2RS)-N-(p-fluorophenyl)glycine 
• 56464-70-1 2-amino-2-(4-fluorophenyl)acetonitrile 
• 321-36-8 2,2,2-trichloro-1-(4-fluorophenyl)ethan-1-one 
• 220130-49-4 [(diphenylmethyl)amino](4-fluorophenyl)acetonitrile 
• 54582-02-4 (+/-)-N-phenylacetyl-p-fluorophenylglycine 
• 1379588-33-6 ethyl 2-(4-fluorophenyl)-2-(hydroxyimino)acetate 
• 1813-94-1 ethyl 4-fluorobenzoylformate 
• 42718-18-3 dl-α-4-fluorophenylglycine methyl ester hydrochloride 
• 1428149-40-9 4-fluoro-(RS)-phenylglycinamide hydrochloride 
• 145057-88-1 2-<(2-hydroxy-1-phenylethyl)amino>-2-(4-fluorophenyl)ethanenitrile 
• 145058-05-5 methyl (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-fluorophenyol)ethanoate 
• 145057-97-2 (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(4-fluorophenyl)ethanoic acid 
• 42718-13-8 α-amino-4-fluorobenzeneacetic acid methyl ester 

Downstream Products

• 168158-39-2 (S)-2-(((benzyloxy)carbonyl)amino)-2-(4-fluorophenyl)acetic acid 
• 174770-74-2 (R)-2-amino-2-(4-fluorophenyl)ethanol 
• 224434-01-9 (S)-1-(4-fluorophenyl)-2-hydroxyethylamine 
• 168158-34-7 (R)-N⁴-Benzyloxy-N¹-[(S)-(4-fluoro-phenyl)-methylcarbamoyl-methyl]-2-isobutyl-succinamide 
• 345579-81-9 (S)-2-Amino-2-(4-fluoro-phenyl)-N-methyl-acetamide 
• 956000-05-8 (S)-N-(tert-butoxycarbonyl)-(4-fluorophenyl)glycinamide 
• 956001-37-9 (S)-tert-butyl (cyano(4-fluorophenyl)methyl)carbamate 
• 785041-04-5 (αS)-α-amino-4-fluoro-benzeneacetamide 
• 936352-69-1 C₂₀H₂₃FN₂O₅S 
• 936352-80-6 C₁₄H₁₂FN₃O₅S 

Relevant academic research and scientific papers

Dutch resolution of racemic 4-hydroxy- and 4-fluorophenylglycine with mixtures of phenylglycine and (+)-10-camphorsulfonic acid

4-Hydroxyphenylglycine and 4-fluorophenylglycine can be resolved with (+)-10-camphorsulfonic acid only if DL- or D-(-)-phenylglycine is added. When using DL-phenylglycine this is co-resolved in this process. In this resolution process mixed crystals are formed of the (+)-10-camphorsulfonic acid salts of the D-(-)-enantiomers of phenylglycine and the para substituted phenylglycines. In the crystal lattice of the mixed salts approximately 25- 30% of the D-(-)-phenylglycine molecules can be randomly replaced by D-(-)- para substituted phenylglycines, resulting in the desired resolution. The overall non-stoichiometric composition of the mixed crystals reflects to some extent the composition in solution. This behaviour is typical for solid solutions. The solid solution behaviour in this so called 'Dutch resolution' is proven by differential scanning calorimetry (DSC), X-ray crystal structure determination and powder diffraction. (C) 2000 Elsevier Science Ltd.

Efficient chemoenzymatic synthesis of (S)-α-amino-4-fluorobenzeneacetic acid using immobilized penicillin amidase

An efficient chemoenzymatic route was developed for synthesis of (S)-α-amino-4-fluorobenzeneacetic acid, a valuable chiral intermediate of Aprepitant, using immobilized penicillin amidase catalyzed kinetic resolution of racemic N-phenylacetyl-4-fluorophen

Synthesis of Air- and Moisture-Stable, Storable Chiral Oxorhenium Complexes and Their Application as Catalysts for the Enantioselective Imine Reduction

Air-/moisture-stable, crystalline, and storable chiral salicyloxazoline based oxorhenium(V) complexes have been synthesized and their catalytic application for the asymmetric reduction of ketimines using hydrosilane as hydride source is disclosed. A broad substrate scope, high yields, and excellent enantioselectivities (up to 99 %) are attained. Furthermore, the syntheses of enantiopure α-amino esters, γ- and δ-lactams, and isoindolinones have also been carried out using this methodology. Finally, the method has been applied to synthetic targets of pharmaceutical relevance, such as R-(+)-salsolidine and R-(+)-crispine A.

Enzymatic synthesis of chiral phenylalanine derivatives by a dynamic kinetic resolution of corresponding amide and nitrile substrates with a multi-enzyme system

Mutant α-amino-ε-caprolactam (ACL) racemase (L19V/L78T) from Achromobacter obae with improved substrate specificity toward phenylalaninamide was obtained by directed evolution. The mutant ACL racemase and thermostable mutant D-amino acid amidase (DaaA) from Ochrobactrum anthropi SV3 co-expressed in Escherichia coli (pACLmut/pDBFB40) were utilized for synthesis of (R)-phenylalanine and non-natural (R)-phenylalanine derivatives (4-OH, 4-F, 3-F, and 2-F-Phe) by dynamic kinetic resolution (DKR). Recombinant E. coli with DaaA and mutant ACL racemase genes catalyzed the synthesis of (R)-phenylalanine with 84% yield and 99% ee from (RS)-phenylalaninamide (400 mM) in 22 h. (R)-Tyrosine and 4-fluoro-(R)-phenylalanine were also efficiently synthesized from the corresponding amide compounds. We also co-expresed two genes encoding mutant ACL racemase and L-amino acid amidase from Brevundimonas diminuta in E. coli and performed the efficient production of various (S)-phenylalanine derivatives. Moreover, 2-aminophenylpropionitrile was converted to (R)-phenylalanine by DKR using a combination of the non-stereoselective nitrile hydratase from recombinamt E. coli and mutant ACL racemase and DaaA from E. coli encoding mutant ACL racemase and DaaA genes. Copyright

A remarkable titanium-catalyzed asymmetric strecker reaction using hydrogen cyanide at room temperature

Close to perfect enantioselectivity (up to 98% ee) is obtained for the formation of amino nitrites using hydrogen cyanide (HCN) as the cyanide source at room temperature for the first time. In an operationally simple process, the catalyst generated from a partially hydrolyzed titanium alkoxide (PHTA) and (S)-N-salicyl-ss-amino alcohol ligand, catalyzes the cyanation of imines in a short reaction time.

Chemoenzymatic approaches to the dynamic kinetic asymmetric synthesis of aromatic amino acids

Enzymatic approaches for the production of amino acids by nitrilases are described. Dynamic kinetic asymmetric synthesis conditions were established for the aromatic aminonitriles, phenylglycinonitrile and 4- fluorophenylglycinonitrile, at high pH to produce the corresponding amino acid products in high enantiomeric excess. N-Acylation of aromatic aminonitriles led to spontaneous racemization at pH 8, allowing preferential enzymatic hydrolysis of the (R)-enantiomer to afford the product N-acylamino acids in up to 99% enantiomeric excess (ee).

A practical asymmetric synthesis of homochiral α-arylglycines

Enantioselective reduction of a series of substituted aryl trichloromethyl ketones with the CBS-catecholborane reagent afforded homochiral aryl trichloromethyl carbinols which have been elaborated to give homochiral α-arylglycines in high e.e.

Polymorphic form of a tachykinin receptor antagonist

This invention is concerned with a novel polymorphic form of the compound 2-(R)-(1-(R)-(3,5-bis(trifluoromethyl)-phenyl)-ethoxy)-3-(S)-(4-fluoro)phenyl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine which is a tachykinin receptor antagonist useful in the treatment or prevention of disorders of the central nervous system, inflammatory diseases, pain or migraine, asthma, and emesis. The instant polymorphic form has advantages over the other known forms of 2-(R)-(1-(R)-(3,5-bis(trifluoro-methyl)-phenyl)ethoxy)-3-(S)-(4-fluoro)phenyl-4-(3-(5-oxo-1H,4H-1,2,4-triazolo)methylmorpholine in terms of thermodynamic stability and suitability for inclusion in pharmaceutical formulations.

MORPHOLINE AND THIOMORPHOLINE TACHYKININ RECEPTOR ANTAGONISTS

Substituted heterocycles of the general structural formula: STR1 are tachykinin receptor antagonists useful in the treatment of inflammatory diseases, pain or migraine, asthma and emesis, and calcium channel blockers useful in the treatment of cardiovascular conditions such as angina, hypertension or ischemia.