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Usage

Uses

Used in Pharmaceutical Industry:
(S)-2-Acetamido-3-(4-nitrophenyl)propanoic acid is used as a key intermediate in the synthesis of non-steroidal anti-inflammatory drugs (NSAIDs) and other pharmaceuticals. Its role in these syntheses is crucial for creating compounds with enhanced biological activity and therapeutic effects, contributing to the development of new medications for various health conditions.
Used in Organic Synthesis:
In the field of organic chemistry, (S)-2-Acetamido-3-(4-nitrophenyl)propanoic acid serves as a versatile building block for the creation of a wide range of organic compounds. Its unique structural features allow it to be incorporated into complex molecular frameworks, facilitating the discovery and production of novel chemical entities with potential applications in various industries.

InChI:InChI=1/C11H12N2O5/c1-7(14)12-10(11(15)16)6-8-2-4-9(5-3-8)13(17)18/h2-5,10H,6H2,1H3,(H,12,14)(H,15,16)/t10-/m0/s1

Upstream product

• 93341-45-8 α-acetylamino-4-nitro-trans-cinnamic acid 
• 2018-61-3 (S)-2-acetylamino-3-phenylpropanoic acid 
• 63-91-2 L-phenylalanine 
• 70973-01-2 2-acetamido-3-(4-nitrophenyl)acrylic acid 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 3235-26-5 2-(N-acetylamino)-2-benzylpropanedioic diethyl ester 
• 6265-87-8 2-acetylamino-2-(4-nitrobenzyl)malonic acid diethyl ester 
• 108-24-7 acetic anhydride 
• 62561-97-1 N-acetyl-4-nitro-DL-phenylalanine 

Downstream Products

• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 402497-81-8 N-acetyl-4-amino-L-phenylalanine 
• 1400930-04-2 C₁₆H₂₁N₃O₆ 
• 76311-21-2 ester methylique de la N-acetyl-p-(methacrylamido acetamido) L-phenylalanine 
• 36097-42-4 2(S)-acetylamino-3-(4-amino-phenyl)-propionic acid methyl ester 
• 60521-91-7 Ac-Phe(4-NHAc)-OMe 
• 864238-27-7 Fmoc-Phe(4-NH₂-3-NO₂)-OH 
• 864238-42-6 D,L-4-Acetamido-N-acetyl-3-nitrophenylalanine methyl ester 
• 898291-08-2 N-methyl-N-(4-chlorobutyl) O-(5-nitrofuryl-2-methyl) N'-(4-(2-((S)-acetylamino-2-carboxy)ethyl))phenyl phosphorodiamidate 
• 898291-06-0 N-methyl-N-(4-chlorobutyl) N'-(4-(2-((S)-acetylamino-2-carboxyallyl)ethyl))phenyl phosphorodiamidic chloride 
• 898291-04-8 N-acetyl-4-amino-L-phenylalanine allyl ester 
• 36097-40-2 (S)-ethyl 2-acetamido-3-(4-nitrophenyl)propanoate 
• 14504-87-1 Ac-p-NO2-L-Phe-Mel-OEt 

Relevant academic research and scientific papers

Self-assembly and nonlinear optical properties of a synthetic dipeptide

The self-assembly propensities and nonlinear optical properties of synthetic dipeptides are illustrated. The single crystal X-ray diffraction study of dipeptide 1 containing a p-nitrophenylalanine moiety reveals that the peptide adopts a supramolecular antiparallel β-sheet structure using hydrogen bonding, as well as π-π stacking interactions, in the solid state and the peptide exhibits nonlocal thermal nonlinear refraction due to the thermal lensing effect. The heat dissipation in the dipeptide 1 was a slow process with a millisecond to microsecond time scale. However the peptide 2 containing a p-nitrophenylacetic acid moiety adopts a parallel β-sheet structure and has no thermal lensing effect.

Synthesis and application of peripherally alkyl-functionalized dendritic pyrphos ligands: Homogeneous-supported catalysts for enantioselective hydrogenation

A new series of dendritic ligands with a chiral diphosphine located at the focal point have been synthesized through coupling of (R,R)-3,4-bis(biphenylphosphino)pyrrolidine (pyrphos) with peripherally alkyl-functionalized benzoic acid dendrons. These ligands were employed in the Rh-catalyzed asymmetric hydrogenation of prochiral dehydroamino acids, exhibiting excellent catalytic activities and enantioselectivities. The second-generation dendritic catalyst could be recovered by simple liquid-liquid biphasic separation and reused four times without serious loss of its activity and selectivity.

Design and synthesis of phosphotyrosine peptidomimetic prodrugs

A novel approach to the intracellular delivery of aryl phosphates has been developed that utilizes a phosphoramidate-based prodrug approach. The prodrugs contain an ester group that undergoes reductive activation intracellularly with concomitant expulsion

A comparison of the asymmetric hydrogenation catalyzed by rhodium complexes containing chiral ligands with a binaphthyl unit and those with a 5,5′,6,6′,7,7′,8,8′-octahydro-binaphthyl unit

The chiral ligands H8-BINAPO and H8-BDPAB were synthesized by reacting chlorodiphenylphosphine with H8-BINOL and H8-BINAM, respectively. Applications of these ligands in the Rh-catalyzed enantioselective hydrogenation of a variety of (Z)-acetamido-3-arylacrylic acid methyl esters provided chiral amino acid derivatives with good to excellent enantioselectivities (H8-BINAPO: up to 84.0% e.e.; H8-BDPAB: up to 97.1% e.e.). In the hydrogenation of acetamidoacrylic acid, 99% e.e. was obtained when a [Rh(H8-BDPAB)]+ catalyst was used. The catalytic activities and enantioselectivities of [Rh(H8-BINAPO)]+ and [Rh(H8-BDPAB]+ are substantially better than those obtained with the corresponding rhodium catalysts containing BINAPO (up to 64% e.e.) and BDPAB (up to 92.6% e.e.).

Method for preparing enantiomeric forms of amino alkylaminophenyl propanoic acid

A process for preparing an enantiomeric form of 2-amino-3-(4-alkylaminophenyl)-propanoic acid of formula (I) or a salt thereof: STR1 in which Alk represents an alkyl radical containing 1 to 2 carbon atoms, from (L)-phenylalanine to obtain the (S)-enantiomer of 2-amino-3-(4-alkylaminophenyl)-propanoic acid, or from (D)-phenylalanine to obtain the (R)-enantiomer of 2-amino-3-(4-alkylaminophenyl)propanoic acid.

Acylase I catalysed hydrolysis of para-substituted (S)-phenylalanine derivatives from mixtures of the racemic ortho- and para-substituted isomers

para-Substituted (S)-phenylalanines may be obtained by treatment of the corresponding mixtures of ortho- and para-substituted N-acetyl-(RS)- phenylalanines with Acylase I from porcine kidney. The selectivity of the enzyme may be attributed to its evolution to digest peptide derivatives of (S)-phenylalanine and (S)-tyrosine.