N-Benzoyl-l-phenylalanine

Base Information

• Chemical Name: N-Benzoyl-l-phenylalanine
• CAS No.: 2566-22-5
• Molecular Formula: C16H15NO3
• Molecular Weight: 269.3
• UNII: 9S304JL9M7
• DSSTox Substance ID: DTXSID701313598
• Nikkaji Number: J231.705B
• Wikidata: Q27162527
• ChEMBL ID: CHEMBL22685
• Mol file: 2566-22-5.mol

Synonyms:benzoylphenylalanine;benzoylphenylalanine, (DL)-isomer;N-benzoyl-D-phenylalanine

Chemical Property of N-Benzoyl-l-phenylalanine

Chemical Property:

• Appearance/Colour: Crystalline
• Vapor Pressure: 5.32E-10mmHg at 25°C
• Melting Point: 184 °C (decomp)
• Refractive Index: 1.569
• Boiling Point: 532 °C at 760 mmHg
• PKA: 3.80±0.10(Predicted)
• Flash Point: 275.5 °C
• PSA: 66.40000
• Density: 1.232 g/cm³
• LogP: 2.50320
• Storage Temp.: Store at RT.
• XLogP3: 2.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 269.10519334
• Heavy Atom Count: 20
• Complexity: 331

Purity/Quality:

98%,99%, ^*data from raw suppliers

Benzoyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn,Xi
• Hazard Codes: Xn,Xi

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC(C(=O)O)NC(=O)C2=CC=CC=C2
• Isomeric SMILES: C1=CC=C(C=C1)C[C@@H](C(=O)O)NC(=O)C2=CC=CC=C2
• Uses: N-Benzoyl-L-phenylalanine is used in the preparation of α-di/monoketo ester derivatives of n-protected amino acids as inhibitors of cysteine of serine proteinases, as well as calpain inhibitors.

Technology Process of N-Benzoyl-l-phenylalanine

There total 115 articles about N-Benzoyl-l-phenylalanine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

(Z)-2-benzamidocinnamic acid (26348-47-0) → DL-N-benzoylphenylalanine (2566-22-5,2901-76-0,37002-52-1)

Guidance literature:

With hydrogen; for 0.00277778h;

DOI:10.1021/acs.jpca.5b06802

Reference yield: 99.0%

Phenylalanine (150-30-1,25191-15-5,658-69-5,67675-33-6) + benzoyl chloride (98-88-4) → DL-N-benzoylphenylalanine (2566-22-5,2901-76-0,37002-52-1)

Guidance literature:

With sodium hydroxide; N-ethyl-N,N-diisopropylamine; In water; 1.) 0 deg C, 30 min; 2.) up to RT, 30 min;

Reference yield: 98.0%

→ DL-N-benzoylphenylalanine (2566-22-5,2901-76-0,37002-52-1)

Guidance literature:

With hydrogen; In methanol; for 72h; under 760 Torr;

DOI:10.1016/S0040-4020(01)82411-X

upstream raw materials:

DL-N-benzoylphenylalanine

L-phenylalanine

benzoyl chloride

benzoic acid N-hydroxysuccinimide ester

Downstream raw materials:

N-(1-benzyl-2-oxo-propyl)-benzamide

methyl (S)-2-(benzoylamino)-3-phenylpropanoate

(S)-ethyl N-benzoyl-phenylalaninate

N-benzoylphenylalanine ethylester

Refernces

• 1、 Doerfler, Dennis L.,Bird, Bruce A.,Campbell, Iain M.. "N-BENZOYLPHENYLALANINE AND N-BENZOYLPHENYLALANINOL, AND THEIR BIOSYNTHESIS IN PENICILLIUM BREVICOMPACTUM". . p. 2303 - 2304. Retrieved 1981.
• 2、 Rahmo, Abdulkader,Fife, Thomas H.. "Inhibition effects in the hydrolysis reactions of esters and peptides catalyzed by carboxypeptidase A: An example of cooperative binding effects with a monomeric enzyme". . p. 226 - 241. Retrieved 2000.
• 3、 Quiros,Parker,Turner. "Tuning lipase enantioselectivity in organic media using solid-state buffers". . p. 5074 - 5079. Retrieved 2001.
• 4、 Chen, Jian,Zhu, Shaolin. "Nickel-Catalyzed Multicomponent Coupling: Synthesis of α-Chiral Ketones by Reductive Hydrocarbonylation of Alkenes". supporting information. p. 14089 - 14096. Retrieved 2021/09/13.
• 5、 Auld, Douglas,Buhrlage, Sara J.,Casalena, Dominick,Chan, Wai Cheung,Dhe-Paganon, Sirano,Hu, Bin,Liu, Xiaoxi,Magin, Robert S.,Marto, Jarrod A.,Roberts, Rebekka M.,Seo, Hyuk-Soo,Varca, Anthony C.,Zhu, He. "Identification and validation of selective deubiquitinase inhibitors". . p. 1758 - 13,1771. Retrieved 2021/12/20.