19817-70-0

Basic information

• Product Name: Alanine, N-benzoyl-3-phenyl-, ethyl ester, DL-
• Synonyms: Alanine, N-benzoyl-3-phenyl-, ethyl ester, DL-;(2S)-2-(benzoylamino)-3-phenyl-propionic acid ethyl ester;(2S)-2-[(oxo-phenylmethyl)amino]-3-phenylpropanoic acid ethyl ester;ethyl (2S)-2-(benzoylamino)-3-phenylpropanoate;ethyl (2S)-2-(benzoylamino)-3-phenyl-propanoate;ethyl (2S)-3-phenyl-2-(phenylcarbonylamino)propanoate;ethyl N-benzoylphenylalaninate;N-Benzoyl-3-phenyl-DL-alanine ethyl ester
• CAS NO: 19817-70-0
• Molecular Formula: C₁₈H₁₉NO₃
• Molecular Weight: 297.36
• Mol File: 19817-70-0.mol
• Article Data: 24

Chemical Properties

• Boiling Point: 505.1°C at 760 mmHg
• Flash Point: 259.3°C
• Appearance: /
• Density: 1.142g/cm³
• Vapor Pressure: 2.51E-10mmHg at 25°C
• Refractive Index: 1.563
• CAS DataBase Reference: Alanine, N-benzoyl-3-phenyl-, ethyl ester, DL-(CAS DataBase Reference)
• NIST Chemistry Reference: Alanine, N-benzoyl-3-phenyl-, ethyl ester, DL-(19817-70-0)
• EPA Substance Registry System: Alanine, N-benzoyl-3-phenyl-, ethyl ester, DL-(19817-70-0)

Safety Data

• Hazardous Substances Data: 19817-70-0(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H19NO3/c1-2-22-18(21)16(13-14-9-5-3-6-10-14)19-17(20)15-11-7-4-8-12-15/h3-12,16H,2,13H2,1H3,(H,19,20)/t16-/m0/s1

Upstream product

• 26348-46-9 (Z)-ethyl 2-benzamido-3-phenylacrylate 
• 64-17-5 ethanol 
• 952524-02-6 (S)-1-benzoyl-2-(α-acetoxyethyl)benzimidazole 
• 1795-96-6 phenylalanine ethyl ester 
• 3081-24-1 H-Phe-OEt 
• 98-88-4 benzoyl chloride 
• 65-85-0 benzoic acid 
• 100-39-0 benzyl bromide 
• 93-97-0 benzoic acid anhydride 
• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 100-52-7 benzaldehyde 
• 63-91-2 L-phenylalanine 
• 100-44-7 benzyl chloride 

Downstream Products

• 1350524-96-7 1-(2-benzamido-3-phenylpropanoyl)-4-phenylthiosemicarbazide 
• 1353566-00-3 C₂₂H₁₉NO₅ 
• 5267-65-2 (S)-N-(1-hydroxy-3-phenylpropan-2-yl)benzamide 
• 511286-63-8 (4S) 3,4-dibenzyl[1,2,3]oxathiazolidine-2,2-dioxide 
• 1349191-55-4 (S)-ethyl-5-(benzylamino)-6-phenyl-hex-2-ynoate 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 118474-25-2 (S)-Bz-Phe-(S)-LeuOMe 
• 128062-21-5 3-(4-Amino-phenyl)-2-benzoylamino-2-benzyl-3-oxo-propionic acid ethyl ester 
• 88406-47-7 N-[(S)-1-(4-Methyl-6-oxo-1,6-dihydro-pyrimidin-2-yl)-2-phenyl-ethyl]-benzamide 
• 23912-50-7 (S)-N-(1-Hydrazineyl-1-oxo-3-phenylpropan-2-yl)benzamide 
• 89311-20-6 N-thiobenzoyl S-phenylalanine ethyl ester 
• 64-17-5 ethanol 

Relevant articles and documents

Synthesis of chiral Rh-bichep complexes, highly efficient catalysts for asymmetric hydrogenations

Chiral cationic and neutral Rh complexes RhX(bichep)(nbd) (X=Cl,ClO4; NBD=norbornadiene;bichep=2,2′-bis(dicyclohexylphosphino)-6,6'-dimethyl-l, r-biphenyl) are highly active and excellent catalysts for enantioselective hydrogenation of prochiral olefms and ketones under mild reaction conditions.

Electrochemical anion pool synthesis of amides with concurrent benzyl ester synthesis

An electrosynthesis method for amide bond formation has been developed in an attempt to increase the atom economy for this class of reactions. This "anion pool" method electrochemically generates strong nucleophiles from amine substrates. The amine nucleophiles then react with acid anhydrides to generate amides, and the by-product from this reaction undergoes further chemical transformations to generate pharmaceutically relevant benzoic esters. These one-pot reactions are operationally simple, are performed at room temperature, and avoid rare transition metals and added bases. The amide synthesis is amenable to primary and secondary amines and a variety of anhydrides with yields up to 90% obtained. Atom economy and process mass index (PMI) values calculated for this procedure indicate that this process can be considered greener compared to traditional amide synthesis routes used by industry. Furthermore, this electrochemical approach showed unique selectivity when substrates that contained two inequivalent amine moieties were examined.

Synthesis and antimicrobial activities of novel sorbic and benzoic acid amide derivatives

A series of sorbic and benzoic acid amide derivatives were synthesized by conjugating sorbic acid (SAAD, a1–a7) or benzoic acid (BAAD b1–b6) with amino acid esters and their antimicrobial activities were investigated against Escherichia coli, Bacillus subtilis and Staphylococcus aureus, mixed bacteria from rancid milk, Saccharomyces cerevisiae, and Aspergillus niger. The antimicrobial activity of sorbic acid amides was better than that of benzoic acid amides. The minimum inhibitory concentrations (MIC) of compound isopropyl N-[1-oxo-2, 4-hexadien-1-yl]-L-phenylalaninate (a7) were 0.17 mM against B. subtilis, and 0.50 mM against S. aureus, while the MIC values of sorbic acid were more than 2 mM respectively. Also, compound a7 displayed pH-independent antimicrobial activity in the range of pH 5.0–9.0 and was effective at pH 9.0. These results demonstrated that the conjugation of sorbic acid with amino acid esters led to significant improvement of in vitro antimicrobial attributes, but little effect was observed for benzoic acid amide derivatives.