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

• 64-17-5 ethanol 
• 2566-22-5 DL-N-benzoylphenylalanine 
• 74923-17-4 methyl N-benzoylphenylalaninate 
• 26348-46-9 (Z)-ethyl 2-benzamido-3-phenylacrylate 
• 1795-96-6 phenylalanine ethyl ester 
• 94-36-0 dibenzoyl peroxide 
• 98-88-4 benzoyl chloride 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 3182-93-2 (L)-phenylalanine ethyl ester hydrochloride 
• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 945986-05-0 2-benzoylamino-2-benzylmalonic acid monoethyl ester 
• 952524-02-6 (S)-1-benzoyl-2-(α-acetoxyethyl)benzimidazole 
• 945986-15-2 C₂₁H₂₃NO₅ 
• 96-86-6 diethyl benzamidomalonate 

Downstream Products

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

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.

Dynamic Kinetic Resolution of Azlactones by a Chiral N, N-Dimethyl-4-aminopyridine Derivative Containing a 1,1′-Binaphthyl Unit: Importance of Amide Groups

A dynamic kinetic resolution (DKR) of azlactones in the presence of benzoic acid and a binaphthyl-based N,N-4-dimethylaminopyridine (DMAP) derivative 1i having two amide groups at the 3,3′-positions of a binaphthyl unit is developed. The reaction proceeded smoothly with a wide range of azlactones to provide α-amino acid derivatives with good to high enantiomeric ratios (er's). A multigram-scale reaction (2.5 g) for the DKR of azlactone 2d was also demonstrated, and the resulting product was converted to unnatural α-amino acid 6d′.