N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester

Base Information

• Chemical Name: N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester
• CAS No.: 73058-37-4
• Molecular Formula: C15H15 N3 O3
• Molecular Weight: 285.302
• UNII: 4HLP399ZJY
• ChEMBL ID: CHEMBL4532899
• Nikkaji Number: J3.646.589A
• Mol file: 73058-37-4.mol

Synonyms:Bortezomib acid methyl ester;4HLP399ZJY;73058-37-4;UNII-4HLP399ZJY;N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester;L-Phenylalanine, N-(2-pyrazinylcarbonyl)-, methyl ester;(S)-Methyl 3-phenyl-2-(pyrazine-2-carboxamido)propanoate;N-Pyrazinylcarbonyl-L-phenylalanine Methyl Ester;N-PYRAZINYLCARBONYLPHENYLALANINE METHYL ESTER;Pyrazine-2-carbonylphenylalanine methyl ester;SCHEMBL2125371;CHEMBL4532899;AGZXSMPTQAISJW-LBPRGKRZSA-N;CS-0163875;N-pyrazineformyl-L-phenylalanine Methyl Ester;(S)-methyl 3-phenyl-2-(pyrazine-2-carboxamido)propanoate? (Bortezomib Impurity pound(c)

Chemical Property of N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester

Chemical Property:

• Melting Point: 55 °C
• Boiling Point: 533.2±50.0 °C(Predicted)
• PKA: 11.75±0.46(Predicted)
• PSA: 81.18000
• Density: 1.238±0.06 g/cm3(Predicted)
• LogP: 1.38160
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• XLogP3: 0.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 285.11134135
• Heavy Atom Count: 21
• Complexity: 356

Purity/Quality:

99%+, ^*data from raw suppliers

N-Pyrazinylcarbonylphenylalanine Methyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: COC(=O)C(CC1=CC=CC=C1)NC(=O)C2=NC=CN=C2
• Isomeric SMILES: COC(=O)[C@H](CC1=CC=CC=C1)NC(=O)C2=NC=CN=C2
• Uses: N-Pyrazinylcarbonyl-L-phenylalanine Methyl Ester can be used for the synthesis of Bortezomib from L-phenylalanine via dipeptidyl boronic acid ester intermediates.

Technology Process of N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester

There total 6 articles about N-(2-Pyrazinylcarbonyl)-L-phenylalanine Methyl Ester 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%

2-pyrazylcarboxylic acid (98-97-5) + methyl (2S)-2-amino-3-phenylpropanoate hydrochloride (7524-50-7) → N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester (73058-37-4)

Guidance literature:

With 4-methyl-morpholine; 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; In dichloromethane; acetonitrile; at -15 - 25 ℃; for 5h; Product distribution / selectivity;

Reference yield: 96.0%

2-pyrazylcarboxylic acid (98-97-5) + methyl (2S)-2-amino-3-phenylpropanoate (2577-90-4) → N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester (73058-37-4)

Guidance literature:

With 2,4-bis(trifluoromethyl)phenylboronic acid; In fluorobenzene; at 85 ℃; for 24h; Molecular sieve;

DOI:10.1039/c8cc02558d

Reference yield:

2-pyrazylcarboxylic acid (98-97-5) + DL-phenylalanine methyl ester (15028-44-1) → methyl (pyrazine-2-carbonyl)phenylalaninate (73058-37-4)

Guidance literature:

With 4-(2-(1,3-dioxa-3a1,8,10-triaza-2,3a,14b-triboradibenzo[fg,op]tetracen-2-yl)phenyl)benzo[c]pyrimido[4,5-e][1,2]azaborinin-6(5H)-ol; In fluorobenzene; at 85 ℃; for 8h; Molecular sieve;

DOI:10.1002/chem.201900715

upstream raw materials:

2-pyrazylcarboxylic acid

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

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

DL-phenylalanine methyl ester

Downstream raw materials:

(S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid

N-(pyrazine-2-yl-carbonyl)-L-phenylalanine sodium salt

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

velcade

Refernces

• 1、 Udutha, Suresh,Borkar, Roshan M.,Shankar,Sony,Jala, Aishwarya,Vamshi Krisna,Kiran Kumar,Misra,Prabhakar,Srinivas. "Stress degradation study of bortezomib: Effect of co-solvent, isolation and characterization of degradation products by UHPLC-Q-TOF-MS/MS and NMR and evaluation of the toxicity of the degradation products". . p. 8178 - 8191. Retrieved 2021/05/21.
• 2、 Ju, Yuan,He, Lihui,Zhou, Yuanzheng,Yang, Tao,Sun, Ke,Song, Rao,Yang, Yang,Li, Chengwei,Sang, Zitai,Bao, Rui,Luo, Youfu. "Discovery of Novel Peptidomimetic Boronate ClpP Inhibitors with Noncanonical Enzyme Mechanism as Potent Virulence Blockers in Vitro and in Vivo". supporting information. p. 3104 - 3119. Retrieved 2020/03/04.