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

Base Information

• Chemical Name: (S)-methyl 4-methyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)pentanoate
• CAS No.: 1194235-11-4
• Molecular Formula: C₂₁H₂₆N₄O₄
• Molecular Weight: 398.462
• Mol file: 1194235-11-4.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 8 articles about (S)-methyl 4-methyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)pentanoate 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: 81.0%

methyl (L)-leucinate hydrochloride (7517-19-3) + (S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid (114457-94-2,1608986-16-8) → (S)-methyl 4-methyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)pentanoate (1194235-11-4)

Guidance literature:

(S)-3-phenyl-2[(pyrazine-2-carbonyl)-amino]propionic acid; With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; at 0 ℃; for 0.5h;

methyl (L)-leucinate hydrochloride; With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 7h;

DOI:10.1016/j.cclet.2021.09.102

Reference yield:

2-pyrazylcarboxylic acid (98-97-5) + (x)C2HF3O2*C16H24N2O3 → (S)-methyl 4-methyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)pentanoate (1194235-11-4)

Guidance literature:

2-pyrazylcarboxylic acid; With 4-methyl-morpholine; isobutyl chloroformate; In tetrahydrofuran; at -10 ℃;

(x)C₂HF₃O₂*C₁₆H₂₄N₂O₃; In tetrahydrofuran; at 20 ℃; for 2h;

With sodium hydrogencarbonate; In water; ethyl acetate;

Reference yield:

N-(2-pyrazinylcarbonyl)-L-phenylalanine methyl ester (73058-37-4) → (S)-methyl 4-methyl-2-((S)-3-phenyl-2-(pyrazine-2-carboxamido)propanamido)pentanoate (1194235-11-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydroxide; water / tetrahydrofuran / 1 h

2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.5 h / 0 °C

2.2: 7 h

With water; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; sodium hydroxide; In tetrahydrofuran; dichloromethane;

DOI:10.1016/j.cclet.2021.09.102

upstream raw materials:

methyl (L)-leucinate hydrochloride

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

2-pyrazylcarboxylic acid

N-tert-butoxycarbonyl-L-phenylalanine

Downstream raw materials:

N-(2-pyrazinecarbonyl)-L-phenylalanine-L-leucine

N₂-[1-benzyl-2-(1-[(1,2-dimethylhydrazino)carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-prazinecarboxamide

N₂-[1-benzyl-2-(1-[(2-cyano-1,2-dimethylhydrazino)carbonyl]-3-methylbutylamino)-2-oxoethyl]-2-pyrazinecarboxamide

Refernces

• 1、 -. "CATHEPSIN S INHIBITORS". Page/Page column 56; 57. . Retrieved 2011/06/25.