100896-07-9

Usage

Uses

Used in Pharmaceutical Industry:
(R)-AMINO-NAPHTHALEN-1-YL-ACETIC ACID is used as a key intermediate in the synthesis of non-steroidal anti-inflammatory drugs (NSAIDs) for its role in producing medications like naproxen. It contributes to the development of drugs that alleviate pain, reduce inflammation, and lower fever.
Used in Research and Chemical Synthesis:
(R)-AMINO-NAPHTHALEN-1-YL-ACETIC ACID is employed as a research compound and in chemical synthesis processes due to its unique properties and potential for further development in various applications. Its anti-inflammatory and analgesic properties make it a valuable tool for scientific exploration and the creation of new pharmaceutical agents.

Upstream product

• 66-77-3 1-naphthaldehyde 
• 127358-11-6 (3R,5R,6S)-4-(tert-Butoxycarbonyl)-5,6-diphenyl-3-(1'-naphthyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 127358-18-3 (3R,5R,6S)-5,6-Diphenyl-3-(1'-naphthyl)-2,3,5,6-tetrahydro-1,4-oxazin-2-one 
• 145058-06-6 methyl (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(1-naphthyl)ethanoate 
• 145057-90-5 (R,S)-2-<(2-hydroxy-1-phenylethyl)amino>-2-(1-naphthyl)ethanenitrile 
• 145057-98-3 (S)-2-<(R)-2-hydroxy-1-phenylethylamino>-2-(1-naphthyl)ethanoic acid 
• 248937-28-2 (R,S)-2-[(2-hydroxy-1-phenylethyl)amino]-2-(1-naphthyl)ethanenitrile 
• 113543-62-7 (+/-)-α-Amino-1-naphthaleneacetonitrile 
• 529489-01-8 (R)-1-naphthylglycine amide 
• 144744-37-6 (3R,5S,6R)-2,3,5,6-Tetrahydro-3-(1-naphthyl)-5,6-diphenyl-1,4-oxazin-2-one 

Downstream Products

• 160289-70-3 (R)-(1-naphthyl)-glycyl-(R)-phenylglycine 
• 127358-21-8 N-(Benzyloxycarbonyl)-D-naphthylglycine 

Relevant academic research and scientific papers

An efficient synthesis of 1-naphthylbis(oxazoline) and exploration of the scope in asymmetric catalysis

Both enantiomers of 1-naphthylglycine were obtained in 99% ee by enzymatic resolution of the corresponding racemic amino acid amide, giving access to the novel ligands (R)- and (S)-naphthylbis(oxazoline). Initial studies provided insight into the scope an

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.

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.

Asymmetric synthesis of arylglycines

The asymmetric synthesis of several arylglycines are reported. The methodology deployed involves either cuprate or Friedel - Crafts couplings to chiral bromoglycinates. The % ee's range from 82 to 94%. Both an oxidative and reductive protocol are employed to unmask the oxazinone chiral auxilliary providing the free α-amino acids.