3005-61-6

Basic information

• Product Name: N-benzoyl-L-phenylalanine methyl ester
• Synonyms: (S)-N-Benzoylphenylalanine methyl ester;Methyl (2S)-2-(benzoylamino)-3-phenylpropanoate;N-Benzoylphenylalanine methyl ester;methyl benzoyl-L-phenylalaninate;(S)-methyl 2-benzamido-3-phenylpropanoate;N-benzoyl-L-phenylalanine methyl ester;Methyl N-benzoyl-L-phenylalaninate;methyl (S)-2-(benzoylamino)-3-phenylpropanoate
• CAS NO: 3005-61-6
• Molecular Formula: C₁₇H₁₇NO₃
• Molecular Weight: 283.32178
• Mol File: 3005-61-6.mol

Chemical Properties

• Melting Point: 83-85℃
• Appearance: solid or liquid
• Density: 1.161
• CAS DataBase Reference: N-benzoyl-L-phenylalanine methyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: N-benzoyl-L-phenylalanine methyl ester(3005-61-6)
• EPA Substance Registry System: N-benzoyl-L-phenylalanine methyl ester(3005-61-6)

Safety Data

• Hazardous Substances Data: 3005-61-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Research and Development:
N-benzoyl-L-phenylalanine methyl ester is utilized as a key building block for the synthesis of peptide-based drugs and other organic compounds, contributing to the advancement of pharmaceutical formulations and therapeutic agents.
Used in Drug Delivery Systems:
In the field of drug delivery, N-benzoyl-L-phenylalanine methyl ester is employed as a component in the design and development of innovative systems aimed at improving the efficacy and targeted delivery of pharmaceutical agents.
Used in Organic Chemistry:
N-benzoyl-L-phenylalanine methyl ester serves as a valuable precursor in organic chemistry for the synthesis of a range of organic compounds, broadening the scope of chemical research and applications.
Used in the Synthesis of Bioactive Molecules:
N-benzoyl-L-phenylalanine methyl ester is used as a precursor for the synthesis of bioactive molecules, which have potential applications in various therapeutic areas, including anti-inflammatory and antioxidant treatments.
Used in Biological Research:
N-benzoyl-L-phenylalanine methyl ester is explored for its potential biological activities, with ongoing studies investigating its effects on anti-inflammatory and antioxidant pathways, which could lead to new insights in medical and health sciences.

Upstream product

• 74923-17-4 methyl N-benzoylphenylalaninate 
• 59490-38-9 N-(p-chlorobenzoyl)phenylalanine methyl ester 
• 27573-05-3 methyl ester of benzoylaminocinnamic acid 
• 23405-15-4 benzoic acid N-hydroxysuccinimide ester 
• 2577-90-4 methyl (2S)-2-amino-3-phenylpropanoate 
• 100-52-7 benzaldehyde 
• 7524-50-7 methyl (2S)-2-amino-3-phenylpropanoate hydrochloride 
• 81912-53-0 4(S)-(methoxycarbonyl)-N-benzoyl-1,3-oxazolidine-2-thione 
• 81925-64-6 methyl 3-benzoyl-2-thioxothiazolidine-4-carboxylate 
• 67-56-1 methanol 
• 5874-61-3 4-benzyl-2-phenyl-2-oxazolin-5-one 
• 842-74-0 4-benzylidene-2-phenyloxazole-5(4H)-one 
• 959-22-8 p-nitrophenylbenzoate 
• 65-85-0 benzoic acid 

Downstream Products

• 64686-60-8 4-benzyl-2-phenyl-5-methoxyoxazole 
• 2566-22-5 N-benzoyl-L-phenylalanine 
• 67-56-1 methanol 
• 72150-35-7 Bz-Phe-NH₂ 
• 1208130-69-1 N-((S)-1-((S)-1-(hydroxyamino)-5-(3-nitroguanidino)-1-oxopentan-2-ylamino)-1-oxo-3-phenylpropan-2-yl) benzamide 
• 25755-94-6 methyl 2,5-diphenyloxazole-4-carboxylate 
• 101602-07-7 methyl (Z)-2-benzamido-3-bromo-3-phenylacrylate 
• 934221-61-1 sodium N-(N-benzoyl-L-phenylalanyl)-O-butyl-L-tyrosinate 
• 1338250-32-0 sodium N-(N-benzoyl-L-phenylalanyl)-O-ethyl-L-tyrosinate 
• 934221-66-6 sodium N-(N-benzoyl-L-phenylalanyl)-O-methyl-L-tyrosinate 

Relevant articles and documents

Part III. COD versus NBD precatalysts. Dramatic difference in the asymmetric hydrogenation of prochiral olefins with five-membered diphosphine Rh-hydrogenation catalysts

Induction periods in the asymmetric hydrogenation of prochiral olefins with five-membered chelates of the type [Rh(PP)(diolefin)]BF4 originate from the parallel-running hydrogenation of the prochiral substrate and the diolefin that enters the s

Metal-Free Selective Modification of Secondary Amides: Application in Late-Stage Diversification of Peptides

Here we solve a long-standing challenge of the site-selective modification of secondary amides and present a simple two-step, metal-free approach to selectively modify a particular secondary amide in molecules containing multiple primary and secondary amides. Density functional theory (DFT) provides insight into the activation of C-N bonds. This study encompasses distinct chemical advances for late-stage modification of peptides thus harnessing the amides for the incorporation of various functional groups into natural and synthetic molecules.

Insights into Fast Amide Couplings in Aqueous Nanomicelles

1-Ethyl-3-(3-(dimethylamino)propyl)-carbodiimide (EDC?HCl) has both lipophilic and hydrophilic regions, causing self-aggregation (also called nanoparticle formation) in an aqueous medium containing PS-750-M amphiphile. Kinetic and proton nuclear magnetic resonance studies were used to probe the effect of different organic bases on the potential nanoparticle formation of EDC?HCl. It also reveals why the pyridine base works better under micellar conditions. The methodology was examined on the multigram scale synthesis of bioactive molecules, where excellent reaction yields were obtained without product epimerization while maintaining a shorter reaction time.

Synthesis of Benzoisoselenazolones via Rh(III)-Catalyzed Direct Annulative Selenation by Using Elemental Selenium

Isoselenazolone derivatives have attracted significant research interest because of their potent therapeutic activities and indispensable applications in organic synthesis. Efficient construction of functionalized isoselenazolone scaffolds is still challenging, and thus new synthetic approaches with improved operational simplicity have been of particular interest. In this manuscript, we introduce a rhodium-catalyzed direct selenium annulation by using stable and tractable elemental selenium. A series of benzamides as well as acrylamides were successfully coupled with selenium under mild reaction conditions, and the obtained isoselenazolones could be pivotal synthetic precursors for several organoselenium compounds. Based on the designed control experiments and X-ray absorption spectroscopy measurements, we propose an unprecedented selenation mechanism involving a highly electrophilic Se(IV) species as the reactive selenium donor. The reaction mechanism was further verified by a computational study.

Fast Amide Couplings in Water: Extraction, Column Chromatography, and Crystallization Not Required

In the micelle of PS-750-M, the presence of 3° amides from the surfactant proline linker mimics dimethylformamide, dimethylacetamide, and N-methyl-2-pyrrolidone. The resultant micellar properties enable extremely fast amide couplings mediated by 1-ethyl-3

Nickel-Catalyzed Asymmetric Hydrogenation of 2-Amidoacrylates

Earth-abundant nickel, coordinated with a suitable chiral bisphosphine ligand, was found to be an efficient catalyst for the asymmetric hydrogenation of 2-amidoacrylates, affording the chiral α-amino acid esters in quantitative yields and excellent enantioselectivity (up to 96 % ee). The active catalyst component was studied by NMR and HRMS, which helped us to realize high catalytic efficiency on a gram scale with a low catalyst loading (S/C=2000). The hydrogenated products could be simply converted into chiral α-amino acids, β-amino alcohols, and their bioactive derivatives. Furthermore, the catalytic mechanism was investigated using deuterium-labeling experiments and computational calculations.

Rational Design of 2-Substituted DMAP- N-oxides as Acyl Transfer Catalysts: Dynamic Kinetic Resolution of Azlactones

A novel concept that conversion of chiral 2-substituted DMAP into its DMAP-N-oxide could significantly enhance the catalytic activity and still be used as an acyl transfer catalyst is presented. A new type of chiral 2-substituted DMAP-N-oxides, derived from l-prolinamides, has been rationally designed, facilely synthesized, and applied in the dynamic kinetic resolution of azlactones. Using simple MeOH as the nucleophile, various l-amino acid derivatives were produced in high yields (up to 98% yield) and enantioselectivities (up to 96% ee). Furthermore, α-deuterium labeled l-phenylalanine derivative was also obtained. Experiments and DFT calculations revealed that in 2-substituted DMAP-N-oxide, the oxygen atom acted as the nucleophilic site and the N-H bond functioned as the H-bond donor. High enantioselectivity of the reaction was governed by steric factors, and the addition of benzoic acid reduced the activation energy by participating in the construction of a H-bond bridge. The theoretical chemical study indicated that only when attack directions of the chiral catalyst were fully considered could the correct calculation results be obtained. This work paves the way for the utilization of the C2 position of the pyridine ring and the development of chiral 2-substituted DMAP-N-oxides as efficient acyl transfer catalysts.

An Efficient Catalytic Amidation of Esters Promoted by N-Heterocyclic Carbenes

An efficient NHC-catalyzed amidation between esters and amines or hydrazines is described. This strategy was tolerant for a wide scope of substrates, affording a series of amides (or hydrazides) in good to excellent yields (60-96%) under simple conditions. The approach was also used to synthesize the pharmaceutically relevant antidepressant moclobemide in 85% yield.

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′.

Identification of 1,5,7-Triazabicyclododecene and Polystyrene-Supported Superbases as Efficient Hydroxylaminolysis Agents of Sterically Hindered and Epimerizable Esters

In modern pharmaceutical research, the need for reliable protocols for the preparation of chemical libraries in a controlled manner is quintessential to driving the Design-Make-Test cycle in drug discovery programs. In this letter, we communicate the iden