14257-84-2

Basic information

• Product Name: N-Acetyl-D-phenylglycine
• Synonyms: N-Acetyl-D-phenylglycine;(αR)-α-(Acetylamino)benzeneacetic acid;(2R)-[Acetylamino]-2-phenylacetic acid;Benzeneacetic acid, a-(acetylaMino)-, (R)-;(R)-2-AcetaMido-2-phenylacetic acid
• CAS NO: 14257-84-2
• Molecular Formula: C₁₀H₁₁NO₃
• Molecular Weight: 193.20
• Mol File: 14257-84-2.mol

Chemical Properties

• Boiling Point: 439.2 °C at 760 mmHg
• Flash Point: 219.4 °C
• Appearance: /
• Density: 1.233
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: N-Acetyl-D-phenylglycine(CAS DataBase Reference)
• NIST Chemistry Reference: N-Acetyl-D-phenylglycine(14257-84-2)
• EPA Substance Registry System: N-Acetyl-D-phenylglycine(14257-84-2)

Safety Data

• Hazardous Substances Data: 14257-84-2(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
N-Acetyl-D-phenylglycine is used as a key building block for the synthesis of various pharmaceuticals, contributing to the development of novel drugs with improved therapeutic properties.
Used in Organic Chemistry:
N-Acetyl-D-phenylglycine is used as a versatile intermediate in the synthesis of a wide range of organic compounds, facilitating the creation of new chemical products with diverse applications.
Used in Medicinal Chemistry:
N-Acetyl-D-phenylglycine is utilized in the exploration of its pharmacological properties and potential therapeutic applications, aiding in the advancement of drug discovery and development processes.

Upstream product

• 75-05-8 acetonitrile 
• 298-12-4 Glyoxilic acid 
• 71-43-2 benzene 
• 60-35-5 acetamide 
• 201230-82-2 carbon monoxide 
• 100-52-7 benzaldehyde 
• 2835-06-5 phenylglycin 
• 131934-09-3 ethyl 2-(hydroxyimino)-2-phenylacetate 
• 36061-00-4 methyl 2-acetamido-2-phenylacetate 
• 14257-84-2 N-acetyl-α-phenylglycine 
• 162247-66-7 2-Methyl-5-oxo-4-phenyl-4,5-dihydro-oxazole-4-carboxylic acid ethyl ester 
• 3076-54-8 phenyllead(IV) triacetate 
• 154614-38-7 (+/-)-N-1-acetyl-1-phenyl-2-propenylamine 
• 14304-68-8 N-Acetyl-α-phenylglycine ethyl ester 

Downstream Products

• 107624-90-8 2-hydroxy-2-phenyl-1-[4]pyridyl-ethanone 
• 14257-84-2 (S)-N-acetyl-2-phenylglycine 
• 2935-35-5 (S)-2-phenylglycine 
• 176861-83-9 [Ni(OH₂)2(C₃H₄N₂)2(CH₃CONHCH(C₆H₅)CO₂)2] 
• 175858-29-4 [Co(OH₂)2(C₃H₄N₂)2(CH₃CONHCH(C₆H₅)CO₂)2] 
• 14257-84-2 (R)-(-)-N-acetylphenylglycine 
• 1233211-32-9 C₁₆H₁₄BrNO₂ 
• 1421693-88-0 C₁₀H₁₀NO₃^(1-)*C₁₆H₃₆N⁽¹⁺⁾ 

Relevant articles and documents

Application of aminoacylase I to the enantioselective resolution of α-amino acid esters and amides

Aminoacylase I from Aspergillus melleus, a readily available and inexpensive enzyme mainly used in the industrial production of enantiopure L-amino acids from their N-acetyl derivatives, is shown to hydrolyze the esters and amides of natural and non-natural amino acids with high enantioselectivity (for the ester hydrolysis, E is up to 76, in case of amides E >300). The reaction rates of amide and ester hydrolysis are comparable, and in some cases these conversions proceeded even faster than 'traditional' aminoacylase- catalyzed hydrolysis of N-acetyl derivatives thus providing new possibilities for the resolution of the corresponding racemates. This novel approach provides an alternative route for the biocatalytic production of optically active amino acids and their derivatives.

Chemical resolution of DL-phenylalanine methyl ester using N-acetyl-D-phenylglycine as resolving agent

An improved method for chemical resolution of DL-phenylalanine methyl ester using N-acetyl-D-phenylglycine as a resolving agent is described. This new resolving agent is readily available, non-toxic and easily recoverable from the insoluble diasteromeric salt. This method was used to obtain D-phenylalanine methyl ester with high optical purity of 98.1% and a high yield of 81.2%.

O-Benzyl derivatives of (S)-(+) and (R)-(-)-2-aminobutan-1-ol as new resolving agents for racemic acids. Practical resolutions of N-acyl derivatives of phenylglycine and 4-hydroxyphenylglycine

Treatment of the readily available (S)-(+) and (R)-(-)-2-aminobutan-1-ol 1 with sodium hydride followed by benzyl chloride, or a substituted benzyl halide, afforded the corresponding O-benzyl bases 2-5 in high yields. These new bases are recommended for the large scale resolution of racemic acids. For instance, they proved efficient for the practical resolution of N-acetylphenylglycine (±)-7, N-acetyl-(4-hyroxylphenyl)glycine (±)-9 and N-chloroacetyl-(4-hydroxyphenyl) glycine (±)-10.

Manganese catalysed asymmetric cis-dihydroxylation with H2O 2

High turnover enantioselective alkene cis-dihydroxylation is achieved with H2O2 catalysed by manganese based complexes containing chiral carboxylato ligands. The Royal Society of Chemistry.

GRANZYME B DIRECTED IMAGING AND THERAPY

Provided herein are heterocyclic compounds useful for imaging Granzyme B. Methods of imaging Granzyme B, combination therapies, and kits comprising the Granzyme B imaging agents are also provided.

Chemo- and Enantioselective Pd/B Hybrid Catalysis for the Construction of Acyclic Quaternary Carbons: Migratory Allylation of O-Allyl Esters to α- C-Allyl Carboxylic Acids

We describe herein the asymmetric synthesis of α-allyl carboxylic acids containing an α-quaternary stereocenter by a chiral hybrid catalyst system comprising palladium and boron complexes. The reaction proceeded through palladium-catalyzed ionization of α,α-disubstituted O-allyl esters for the generation of chiral π-allyl palladium complex as an electrophile, boron-catalyzed enolization of the carboxylate part for the generation of chiral α,α-disubstituted carboxylic acid-derived enolates as a nucleophile, and enantioselective coupling between the thus-generated nucleophile and electrophile. Proper combinations of chiral ligands for the boron and palladium catalysts were crucial. The reaction proceeded chemoselectively at the α-position of the carboxylic acid group.

Regiodivergent Enantioselective γ-Additions of Oxazolones to 2,3-Butadienoates Catalyzed by Phosphines: Synthesis of α,α-Disubstituted α-Amino Acids and N,O-Acetal Derivatives

Phosphine-catalyzed regiodivergent enantioselective C-2- and C-4-selective γ-additions of oxazolones to 2,3-butadienoates have been developed. The C-4-selective γ-addition of oxazolones occurred in a highly enantioselective manner when 2-aryl-4-alkyloxazol-5-(4H)-ones were employed as pronucleophiles. With the employment of 2-alkyl-4-aryloxazol-5-(4H)-ones as the donor, C-2-selective γ-addition of oxazolones took place in a highly enantioselective manner. The C-4-selective adducts provided rapid access to optically enriched α,α-disubstituted α-amino acid derivatives, and the C-2-selective products led to facile synthesis of chiral N,O-acetals and γ-lactols. Theoretical studies via DFT calculations suggested that the origin of the observed regioselectivity was due to the distortion energy that resulted from the interaction between the nucleophilic oxazolide and the electrophilic phosphonium intermediate.

Convenient method for reduction of C-N double bonds in oximes, imines, and hydrazones using sodium Borohydride-Raney ni system

(Chemical Equation Presented) A practical method has been developed for reduction of C-N double bond in oximes, imines, and hydrazones with sodium borohydride catalyzed by Raney Ni. The reactions were carried out in basic aqueous solution, and the desired products were obtained in moderate yields after a simple procedure. This method can be applied to synthesize simpler aliphatic or aromatic amines and its analogs. Copyright Taylor & Francis Group, LLC.

Synthesis, enantioresolution, and activity profile of chiral 6-methyl-2,4-disubstituted pyridazin-3(2H)-ones as potent N-formyl peptide receptor agonists

A series of chiral pyridazin-3(2H)-ones was synthesized, separated as pure enantiomers, and evaluated for N-formyl peptide receptor (FPR) agonist activity. Characterization of the purified enantiomers using combined chiral HPLC and chiroptical studies (circular dichroism, allowed unambiguous assignment of the absolute configuration for each pair of enantiomers). Evaluation of the ability of racemic mixtures and purified enantiomers to stimulate intracellular Ca 2+ flux in FPR-transfected HL-60 cells and human neutrophils and to induce β-arrestin recruitment in FPR-transfected CHO-K1 cells showed that many enantiomers were potent agonists, inducing responses in the sub-micromolar to nanomolar range. Furthermore, FPRs exhibited enantiomer selectivity, generally preferring the R-(-)-forms over the S-(+)-enantiomers. Finally, we found that elongation of the carbon chain in the chiral center of the active compounds generally increased biological activity. Thus, these studies provide important new information regarding molecular features involved in FPR ligand preference and report the identification of a novel series of FPR agonists.

Efficient kinetic resolution of amino acids catalyzed by lipase AS 'Amano' via cleavage of an amide bond

Herein the efficient kinetic resolution of non-natural alpha-amino acids catalyzed by lipase AS 'Amano' via cleaving the amide bond is reported. The starting materials were the corresponding amino acid amides and the amino acids were generated with ees of up to 99% with E values of >600. These results indicated that the lipase AS 'Amano' could be a powerful amide hydrolase for the kinetic resolution of amino acid starting from the corresponding amino acid amides.