N-(2-Cyanoethyl)valine

Base Information

• Chemical Name: N-(2-Cyanoethyl)valine
• CAS No.: 51078-49-0
• Molecular Formula: C8H14N2O2
• Molecular Weight: 170.211
• DSSTox Substance ID: DTXSID90470238
• Nikkaji Number: J624.918C
• Mol file: 51078-49-0.mol

Synonyms:N-(2-cyanoethyl)Val;N-(2-cyanoethyl)valine;N-2-cyanoethylvaline

Chemical Property of N-(2-Cyanoethyl)valine

Chemical Property:

• Melting Point: 245-247°C (Sublime)
• Boiling Point: 338.8±27.0 °C(Predicted)
• PKA: 2.24±0.13(Predicted)
• PSA: 73.12000
• Density: 1.076±0.06 g/cm3(Predicted)
• LogP: 0.98978
• Storage Temp.: Refrigerator
• Solubility.: Aqueous Acid (Slightly), DMSO (Slightly)
• XLogP3: -1.8
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 170.105527694
• Heavy Atom Count: 12
• Complexity: 193

Purity/Quality:

99% ^*data from raw suppliers

N-(2-Cyanoethyl)-L-valine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)C(C(=O)O)NCCC#N
• Isomeric SMILES: CC(C)[C@@H](C(=O)O)NCCC#N
• Uses: A metabolite of Acrylonitrile.

Technology Process of N-(2-Cyanoethyl)valine

There total 1 articles about N-(2-Cyanoethyl)valine 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: 91.0%

L-valine (72-18-4,25609-85-2,7004-03-7,921-10-8) + acrylonitrile (107-13-1,25014-41-9) → N-(2-cyanoethyl)-L-valine (51078-49-0)

Guidance literature:

L-valine; With potassium hydroxide; In water; at 20 ℃;

acrylonitrile; In water; at 0 - 5 ℃; for 4.5 - 5.5h;

Reference yield:

N-(2-cyanoethyl)-L-valine (51078-49-0) → (S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid (192725-50-1)

Guidance literature:

Multi-step reaction with 3 steps

1: sodium hydroxide / water / pH 9.5 - 10.5

2: ammonia; hydrogen / methanol / 10 h / 50 °C

3: sodium hydroxide / water / 98 - 100 °C

With ammonia; hydrogen; sodium hydroxide; In methanol; water;

DOI:10.14233/ajchem.2021.22954

Reference yield:

N-(2-cyanoethyl)-L-valine (51078-49-0) → lopinavir (192725-17-0,1798014-18-2)

Guidance literature:

Multi-step reaction with 6 steps

1.1: sodium hydroxide / water / pH 9.5 - 10.5

2.1: ammonia; hydrogen / methanol / 10 h / 50 °C

3.1: sodium hydroxide / water / 98 - 100 °C

4.1: 1,1'-carbonyldiimidazole / ethyl acetate / 2 h / 15 - 20 °C

4.2: 4 h / 70 - 75 °C

5.1: 5%-palladium/activated carbon; ammonium formate / methanol / 2 h / 50 - 55 °C

6.1: sodium hydrogencarbonate / water; ethyl acetate / 0.5 h / 10 - 15 °C

With 5%-palladium/activated carbon; ammonia; hydrogen; ammonium formate; sodium hydrogencarbonate; 1,1'-carbonyldiimidazole; sodium hydroxide; In methanol; water; ethyl acetate;

DOI:10.14233/ajchem.2021.22954

upstream raw materials:

L-valine

acrylonitrile

Downstream raw materials:

(S)-tetrahydro-α-(1-methylethyl)-2-oxo-1(2H)-pyrimidineacetic acid

lopinavir

Refernces

• 1、 Reddy, Peketi Rajesh,Musunuri, Sivanadh,Ramasekhara Reddy,Subrahmanyam Chittala,Murthy,Krishnamohan. "Synthesis and characterization of novel analogues of lopinavir". . p. 151 - 158. Retrieved 2021/01/06.
• 2、 -. "Hydrochloride crystal form of bicyclic ROR[gamma] inhibitor". Paragraph 0088-0089; 0114-0118. . Retrieved 2020/08/18.