(2R)-2-(2-oxopyrrolidin-1-yl)butanamide

Base Information

• Chemical Name: (2R)-2-(2-oxopyrrolidin-1-yl)butanamide
• CAS No.: 103765-01-1
• Molecular Formula: C₈H₁₄N₂O₂
• Molecular Weight: 170.211
• European Community (EC) Number: 642-991-8
• UNII: 73HC18Y1LW
• DSSTox Substance ID: DTXSID10146044
• Nikkaji Number: J1.380.981J
• Wikidata: Q99147555
• ChEMBL ID: CHEMBL150361
• Mol file: 103765-01-1.mol

Synonyms:alpha ethyl 2 oxo 1 Pyrrolidineacetamide;alpha-ethyl-2-oxo-1-pyrrolidineacetamide;etiracetam;Etiracetam, (R)-;Etiracetam, R isomer;etiracetam, R-isomer;Etiracetam, S isomer;etiracetam, S-isomer;Keppra;levetiracetam;R-isomer Etiracetam;S-isomer Etiracetam;UCB 6474;ucb L059;ucb L060;UCB-6474;ucb-L059;ucb-L060;UCB6474;UcbL060

Chemical Property of (2R)-2-(2-oxopyrrolidin-1-yl)butanamide

Chemical Property:

• Melting Point: 114-116 °C(Solv: acetone (67-64-1))
• Boiling Point: 395.9±25.0 °C(Predicted)
• PKA: 15.74±0.50(Predicted)
• PSA: 64.39000
• Density: 1.168±0.06 g/cm3(Predicted)
• LogP: 0.96030
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility.: Acetone (Sparingly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 170.105527694
• Heavy Atom Count: 12
• Complexity: 203

Purity/Quality:

97% ^*data from raw suppliers

(R)-Levetiracetam ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(C(=O)N)N1CCCC1=O
• Isomeric SMILES: CC[C@H](C(=O)N)N1CCCC1=O
• Uses: (R)-Levetiracetam [REV] (Levetiracetam EP Impurity D), is the enantiomer to Levetiracetam [LEV] (L331500), the antiepileptic drug that is highly enantioselective. It is apparent that [LEV] is more potent than [REV] in terms of antiepileptic potency.

Technology Process of (2R)-2-(2-oxopyrrolidin-1-yl)butanamide

There total 6 articles about (2R)-2-(2-oxopyrrolidin-1-yl)butanamide 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: 76.0%

2-(pyrrolidin-1-yl)butanamide → α-ethyl-2-oxo-1-pyrrolidineacetamide (102767-28-2,103765-01-1,103833-73-4,33996-58-6) + C8H16N2O2

Guidance literature:

With sodium periodate; ruthenium(IV) oxide hydrate; In ethyl acetate; at 20 ℃; for 0.5h; Sonication;

Reference yield: 66.0%

α-ethyl-2-oxo-1-pyrrolidineacetic acid, (67118-31-4) → α-ethyl-2-oxo-1-pyrrolidineacetamide (102767-28-2,103765-01-1,103833-73-4,33996-58-6)

Guidance literature:

α-ethyl-2-oxo-1-pyrrolidineacetic acid,; With chloroformic acid ethyl ester; triethylamine; In tetrahydrofuran; at 0 ℃; for 0.5h;

With ammonium hydroxide; In tetrahydrofuran; water; at 20 ℃; for 16h;

DOI:10.1016/j.tetasy.2005.10.014

Reference yield: 17.0%

(S)-(-)-α-ethyl-2-oxo-1-pyrrolidineacetamide → α-ethyl-2-oxo-1-pyrrolidineacetamide (102767-28-2,103765-01-1,103833-73-4,33996-58-6)

Guidance literature:

With sodium hydroxide; Electrochemical reaction;

DOI:10.1039/d0gc03358h

upstream raw materials:

α-ethyl-2-oxo-1-pyrrolidineacetic acid,

levetiracetam

Downstream raw materials:

C₈H₈O₃*C₈H₁₄N₂O₂