145232-47-9

Usage

Uses

Used in Pharmaceutical Drug Synthesis:
(S)-2-Amino-2-methyl-3-(2'-naphthyl)propansaeure is used as a key intermediate in the pharmaceutical industry for the synthesis of various drugs. Its unique structure allows it to serve as a building block for creating more complex molecules with potential therapeutic applications.
Used in Medicinal Chemistry and Drug Development:
In the field of medicinal chemistry, (S)-2-Amino-2-methyl-3-(2'-naphthyl)propansaeure is utilized as a starting material for the development of new drugs. Its chiral nature and structural properties make it a promising candidate for designing novel molecules with specific biological activities.
Used in Organic Compound Synthesis:
(S)-2-Amino-2-methyl-3-(2'-naphthyl)propansaeure is also used as a versatile building block in the synthesis of a wide range of organic compounds. Its unique structure and reactivity enable the creation of diverse molecules with various applications in different industries.
Used in Biological Research:
Due to its potential biological activities, (S)-2-Amino-2-methyl-3-(2'-naphthyl)propansaeure may be employed in biological research to study its interactions with biological systems and to explore its possible roles in various biological processes. This could lead to the discovery of new therapeutic targets and applications in medicine.

Upstream product

• 78761-20-3 ethyl (S)-2-amino-2-methyl-3-naphthalen-2-ylpropanoate 
• 939-26-4 2-bromomethylnaphthyl bromide 
• 65484-51-7 (4S)-4-Methyl-4-(2''-naphthylmethyl)-1-<(S)-1'-phenylethyl>-2-imidazolin-5-on 

Relevant academic research and scientific papers

Mitsunobu approach to the synthesis of optically active α,α-disubstituted amino acids

Chiral tertiary α-hydroxy esters of known stereochemical configuration were transformed to α-azido esters by Mitsunobu reaction with HN3. Optimization of this reaction was shown to proceed at room temperature with high chemical yield using 1,1-(azodicarbonyl)dipiperidine (ADDP) and trimethylphosphine (PMe3). Complete inversion of configuration was observed at the α-carbon. Several α,α- disubstituted amino acids were synthesized in high overall chemical yield and optical purity.

Asymmetric Syntheses via Heterocyclic Intermediates, IV. - Asymmetric Synthesis of α-Methylphenylalanine and its Analogues by Alkylation of 1-chiral Substituted 4-Methyl-2-imidazoline-5-one

Treatment of 2-isocyano-N-propionamide (3a) with butyllithium or potassium tert-butoxide (-70 deg C, tetrahydrofuran) initially causes metalation and subsequent (at ca. -20 deg C) cyclization to give the anionized 4-methyl-1--2-imidazolin-5-one (8).This reacts with benzyl or heterobenzyl halides to yield (4S)-4-benzyl- or (4S)-4-heterobenzyl-4-methyl-1--2-imidazolin-5-ones 9 with an asymmetric induction (d.e. = diastereomeric excess) >>95percent.Hydrolysis of 9 gives α-methylphenylalanine or its analogues of type 11 (nearly optically pure) which have been characterized as their N-acetyl derivatives 12.More over, (S)-1-phenylethylamine (2a), the chiral auxiliary compound, is recovered. - With non-benzylic alkyl halides d.e. is much lower (i.e. with allyl bromide 17percent, with cyclohexylmethyl iodide 35percent). - A model concept for the asymmetric induction which also explains the extremely high asymmetric induction with benzyl halides is proposed. - Methods for the synthesis of 2- unsubstituted 4-alkyl-2-imidazolin-5-ones (type 9a, 15-17) and 2-substituted 4-alkyl-2-imidazolin-5-ones (type 18-20) are described. - The X-ray analysis of 4-benzyl-4-methyl-1-(1'-phenylethyl)-2-imidazolin-5-one (9b) shows a) the "phenyl inside conformation" (folded conformation) for the C-4-benzyl group and b) C-1' fixed in such a way that the hydrogen atom of the phenylethyl group lies in the heterocyclic plane, pointing towards the carbonyl oxygen.