(S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID

Base Information

• Chemical Name: (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID
• CAS No.: 114457-94-2
• Molecular Formula: C14H13N3O3
• Molecular Weight: 271.276
• Hs Code.: 2934999090
• Mol file: 114457-94-2.mol

Synonyms:(S)-3-Phenyl-2-[(pyrazin-2-ylcarbonyl)amino] propanoic acid;

Chemical Property of (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID

Chemical Property:

• Vapor Pressure: 5.27E-14mmHg at 25°C
• Melting Point: 166-169℃
• Refractive Index: 1.612
• Boiling Point: 573.8 °C at 760 mmHg
• PKA: 13.93±0.46(Predicted)
• Flash Point: 300.8 °C
• PSA: 92.18000
• Density: 1.323 g/cm³
• LogP: 1.29320
• Storage Temp.: Sealed in dry,Room Temperature
• Solubility.: DMSO, Methanol (Sparingly)

Purity/Quality:

99%min ^*data from raw suppliers

N-Pyrazinylcarbonyl-L-phenylalanine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID is used for the synthesis of Bortezomib (B675700) from L-phenylalanine via dipeptidyl boronic acid ester intermediates.

Technology Process of (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID

There total 20 articles about (S)-3-PHENYL-2-[(PYRAZIN-2-YLCARBONYL)AMINO] PROPANOIC ACID 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: 99.0%

(pyrazine-2-carbonyl)-L-phenylalanine ethyl ester → (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8)

Guidance literature:

With sodium hydroxide; In water; acetone; at 0 ℃; for 2h;

DOI:10.1021/acs.orglett.9b00584

Reference yield: 98.0%

L-phenylalanine (63-91-2,25191-15-5,658-69-5,67675-33-6) + (1H-benzo[d][1,2,3]triazol-1-yl)(pyrazin-2-yl)methanone (306990-94-3) → (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8)

Guidance literature:

With trialkylamine; In water; acetonitrile; at 20 ℃;

DOI:10.1039/c9ra03380g

Reference yield: 97.0%

N,O-bis(trimethylsilyl)phenylalanine (7364-51-4) + pyrazinecarboxylic acid imidazolide (103435-88-7) → (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8)

Guidance literature:

N,O-bis(trimethylsilyl)phenylalanine; pyrazinecarboxylic acid imidazolide; In dichloromethane; at -40 - 20 ℃; for 19.5h;

With water; citric acid; In dichloromethane;

DOI:10.1016/j.tet.2009.06.042

upstream raw materials:

velcade

N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester

2-pyrazylcarboxylic acid

methyl (2S)-2-amino-3-phenylpropanoate hydrochloride

Downstream raw materials:

N-[(1S)-1[[[(1R)-1-[(3aS,4S,6S,7aR)-hexahydro-3a,5,5-trimethyl-4,6-methano-1,3,2-benzodioxaborol-2-yl]-3-methylbutyl]amino]carbonyl]-2-benzyl]2-pyrazine carboxamide

(S)-methyl 4-methyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)pentanoate

(S)-methyl 3-phenyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)-propanoate

N-pyrazineformyl-L-phenylalanyl-L-tyrosine methyl ester

Refernces

• 1、 Verdoes, Martijn,Florea, Bogdan I.,Van Der Linden, Wouter A.,Renou, Didier,Van Den Nieuwendijk, Adrianus M. C. H.,Van Der Marel, Gijs A.,Overkleeft, Herman S.. "Mixing of peptides and electrophilic traps gives rise to potent, broad-spectrum proteasome inhibitors". . p. 1416 - 1426. Retrieved 2007.
• 2、 Wu, Sara,Waugh, Wanda,Stella, Valentino J.. "Degradation pathways of a peptide boronic acid derivative, 2-Pyz-(CO)-Phe-Leu-B(OH)2". . p. 758 - 765. Retrieved 2000.
• 3、 Kingsley, Laura J.,He, Xiaohui,McNeill, Matthew,Nelson, John,Nikulin, Victor,Ma, Zhiwei,Lu, Wenshuo,Zhou, Vicki W.,Manuia, Mari,Kreusch, Andreas,Gao, Mu-Yun,Witmer, Darbi,Vaillancourt, Mei-Ting,Lu, Min,Greenblatt, Sarah,Lee, Christian,Vashisht, Ajay,Bender, Steven,Spraggon, Glen,Michellys, Pierre-Yves,Jia, Yong,Haling, Jacob R.,Lelais, Gérald. "Structure-Based Design of Selective LONP1 Inhibitors for Probing in Vitro Biology". . p. 4857 - 4869. Retrieved 2021/05/07.
• 4、 Lü, Zirui,Li, Xiaona,Niu, Yan,Sun, Qi,Wang, Chao,Xi, Dandan,Xu, Fengrong,Xu, Ping,Zhou, Tongliang. "Design and synthesis of tripeptidyl furylketones as selective inhibitors against the β5 subunit of human 20S proteasome". . . Retrieved 2020/03/10.