103765-01-1

Basic information

• Product Name: (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE
• Synonyms: 1-PYRROLIDINEACETAMIDE, A-ETHYL-2-OXO-, (AR)-;R-(+)-ETIRACETAM;UCB-L 060;(R)-alpha-Ethyl-2-oxo-1-pyrrolidineacetamide;1-Pyrrolidineacetamide, alpha-ethyl-2-oxo-, (R)-;R-(+)-LevetiracetaM;LevetiracetaM IMpurity D;levetiraccetam R-isomer
• CAS NO: 103765-01-1
• Molecular Formula: C₈H₁₄N₂O₂
• Molecular Weight: 170.20900
• Mol File: 103765-01-1.mol
• Article Data: 9

Chemical Properties

• Melting Point: 114-116 °C(Solv: acetone (67-64-1))
• Boiling Point: 395.9±25.0 °C(Predicted)
• Appearance: /
• Density: 1.168±0.06 g/cm3(Predicted)
• Storage Temp.: Hygroscopic, -20°C Freezer, Under inert atmosphere
• Solubility: Acetone (Sparingly, Sonicated), Chloroform (Slightly), Methanol (Slightly)
• PKA: 15.74±0.50(Predicted)
• CAS DataBase Reference: (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE(103765-01-1)
• EPA Substance Registry System: (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE(103765-01-1)

Safety Data

• Hazardous Substances Data: 103765-01-1(Hazardous Substances Data)

Usage

Description

(R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE, also known as Levetiracetam [REV] (Levetiracetam EP Impurity D), is the enantiomer to Levetiracetam [LEV] (L331500), which is an antiepileptic drug. (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE is characterized by its chiral center, which gives it distinct properties compared to its counterpart, Levetiracetam [LEV].

Uses

Used in Pharmaceutical Industry:
(R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE is used as an impurity in the development and manufacturing process of Levetiracetam [LEV], the antiepileptic drug. Its presence is crucial for ensuring the enantiomeric purity and potency of the final drug product, as [LEV] is more effective in treating epilepsy compared to [REV].
Used in Research and Development:
In the field of pharmaceutical research and development, (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE serves as a valuable compound for studying the differences in biological activity between enantiomers. This knowledge can be applied to the design and synthesis of more effective drugs with fewer side effects.
Used in Quality Control:
(R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE is used in the quality control processes of pharmaceutical companies to ensure that the enantiomeric purity of Levetiracetam [LEV] meets the required standards. This is important for maintaining the safety and efficacy of the drug.
Used in Regulatory Compliance:
In the regulatory compliance industry, (R)-2-(2-OXO-PYRROLIDIN-1-YL)-BUTYRAMIDE is used to establish and verify the enantiomeric purity of Levetiracetam [LEV] as per the guidelines set by regulatory authorities. This ensures that the drug meets the necessary quality and safety standards before it is approved for use in patients.

Upstream product

• 102767-28-2 levetiracetam 
• 67118-31-4 α-ethyl-2-oxo-1-pyrrolidineacetic acid, 

Downstream Products

• 1351861-13-6 C₈H₈O₃*C₈H₁₄N₂O₂ 

Relevant articles and documents

REGIOSELECTIVE OXIDATION OF HETEROCYCLIC ALPHA-AMINO AMIDES

The present invention relates to regioselective chemical and electrochemical processes for the preparation of an oxidized heterocyclic alpha-amino amide compounds. By applying specific catalysts or catalyst systems during chemical oxidation or by applying particular electrochemical oxidation conditions the present invention provides access to valuable alpha amino amide compounds, which are oxidized at the heterocyclic amino group by regioselective introduction of either a hydroxyl or a keto group. In a more particular embodiment, the present invention describes a chemical oxidation reaction, which advantageously is applicable in the enantioselective synthesis of valuable oxidized heterocyclic alpha-amino amide compounds, like levetiracetam, brivaracetam or the synthesis of piracetam. Another aspect of the present invention relates to a process for the electrochemical recycling of alkali perhalogenate oxidants as spent during said regioselective oxidation reactions of the invention. Still another aspect of the invention relates to the electrochemical preparation of perhalogenates.

Ionic Cocrystals of Etiracetam and Levetiracetam: The Importance of Chirality for Ionic Cocrystals

A striking variety of anhydrous and hydrated ionic cocrystals (ICCs) of the enantiopure antiepileptic drug (AED) levetiracetam and of its racemic intermediate etiracetam with the pharmaceutically acceptable salts CaCl2 and MgCl2 was synthesized and structurally characterized. The difference in the interaction of enantiopure and racemic compounds of interest with the inorganic salts was investigated. Variable-temperature X-ray powder diffraction (VT-XRPD) and calorimetric analyses (TGA and DSC) of all obtained ICCs showed a significant improvement in thermal stability with respect to pure racetams.

Ugi Four-Center Three-Component Reaction as a Direct Approach to Racetams

We report the synthesis of racetams, a diverse class of small molecule drugs, by means of the Ugi four-center three-component reaction (U4C-3CR). For the first time, γ-aminobutyric acid is employed as bifunctional input in the Ugi reaction. This protocol is simple, general, and allows one-pot access to a range of drugs and bioactive small molecules.