(S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid

Base Information

• Chemical Name: (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid
• CAS No.: 848777-30-0
• Molecular Formula: C13H17N3O3
• Molecular Weight: 263.296
• Mol file: 848777-30-0.mol

Synonyms:Cyclohexaneacetic acid, α-[(2-pyrazinylcarbonyl)amino]-, (αS)-;

Chemical Property of (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid

Chemical Property:

• Boiling Point: 549.9±40.0 °C(Predicted)
• PKA: 3.09±0.10(Predicted)
• PSA: 95.67000
• Density: 1.266
• LogP: 1.81470

Purity/Quality:

98%Min ^*data from raw suppliers

(S)-2-Cyclohexyl-2-(pyrazine-2-carboxamido)aceticacid 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic acid

There total 5 articles about (S)-2-cyclohexyl-2-(pyrazine-2-carboxaMido)acetic 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: 95.0%

(S)-methyl 2-cyclohexyl-2-(pyrazine-2-carboxamido)acetate (848777-29-7) → (2S)-cyclohexyl[(pyrazin-2-ylcarbonyl)amino]ethanoic acid (848777-30-0)

Guidance literature:

With water; sodium hydroxide; In tetrahydrofuran; methanol; at 20 ℃;

DOI:10.1039/c0cc02823a

Reference yield:

2-pyrazylcarboxylic acid (98-97-5) + L-α-cyclohexylglycine potassium salt (1454838-80-2) → (2S)-cyclohexyl[(pyrazin-2-ylcarbonyl)amino]ethanoic acid (848777-30-0)

Guidance literature:

2-pyrazylcarboxylic acid; With 1,1'-carbonyldiimidazole; In tetrahydrofuran; at 55 - 60 ℃; Inert atmosphere;

L-α-cyclohexylglycine potassium salt; In tetrahydrofuran; tert-butyl alcohol; at 20 ℃; Inert atmosphere;

Reference yield:

2-pyrazylcarboxylic acid (98-97-5) → (2S)-cyclohexyl[(pyrazin-2-ylcarbonyl)amino]ethanoic acid (848777-30-0)

Guidance literature:

Multi-step reaction with 2 steps

1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

2: lithium hydroxide / tetrahydrofuran; water / 3 h / 0 °C

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide; In tetrahydrofuran; water; N,N-dimethyl-formamide;

DOI:10.1021/jm200460q

upstream raw materials:

(S)-methyl 2-cyclohexyl-2-(pyrazine-2-carboxamido)acetate

2-pyrazylcarboxylic acid

(S)-amino(cyclohexyl)acetic acid methyl ester

L-α-cyclohexylglycine potassium salt

Downstream raw materials:

C₂₈H₄₁N₅O₅

C₃₃H₄₁N₅O₅

(S)-tert-butyl 2-((S)-2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)-4-methylpentanoate

(S)-tert-butyl 2-(2-cyclohexyl-2-(pyrazine-2-carboxamido)acetamido)acetate

Refernces

• 1、 -. "PROCESS FOR THE PREPARATION OF INTERMEDIATES USEFUL IN THE PREPARATION OF A VIRAL PROTEASE INHIBITOR". Page/Page column 14. . Retrieved 2013/09/26.
• 2、 Milo, Lawrence J.,Lai, Jack H.,Wu, Wengen,Liu, Yuxin,Maw, Hlaing,Li, Youhua,Jin, Zhiping,Shu, Ying,Poplawski, Sarah E.,Wu, Yong,Sanford, David G.,Sudmeier, James L.,Bachovchin, William W.. "Chemical and biological evaluation of dipeptidyl boronic acid proteasome inhibitors for use in prodrugs and pro-soft drugs targeting solid tumors". experimental part. p. 4365 - 4377. Retrieved 2011/09/15.