88929-35-5

Basic information

• Product Name: Oxiracetam
• Synonyms: Pyrrolidineacetamide, 4-hydroxy-2-oxo-, (4S)-;(S)-4-Hydroxy-2-oxo-1-pyrrolidineacetamide;1-Pyrrolidineacetamide, 4-hydroxy-2-oxo-, (S)-;(4S)-4-Hydroxy-2-oxo-1-pyrrolidineacetaMide;Oxiracetam (mix);1-Pyrrolidineacetamide, 4-hydroxy-2-oxo-, (4S)-;2-[(4S)-4-hydroxy-2-oxopyrrolidin-1-yl]acetamide
• CAS NO: 88929-35-5
• Molecular Formula: C₆H₁₀N₂O₃
• Molecular Weight: 158.1552
• EINECS: 200-429-5
• Product Categories: APIs;Drug Intermediates;Amines;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
• Mol File: 88929-35-5.mol
• Article Data: 17

Chemical Properties

• Melting Point: 135-136℃
• Boiling Point: 494.6 °C at 760 mmHg
• Flash Point: 252.9 °C
• Appearance: /
• Density: 1.416±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 7.39E-12mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: Sealed in dry,Room Temperature
• CAS DataBase Reference: Oxiracetam(CAS DataBase Reference)
• NIST Chemistry Reference: Oxiracetam(88929-35-5)
• EPA Substance Registry System: Oxiracetam(88929-35-5)

Safety Data

• Hazard Codes: Xi:Irritant
• Statements: 36/38
• Safety Statements: 26-36
• Hazardous Substances Data: 88929-35-5(Hazardous Substances Data)

Usage

Uses

An oxiracetam (O846905) enantiomer classified as an effective nootropic.

InChI:InChI=1/C6H10N2O3/c7-5(10)3-8-2-4(9)1-6(8)11/h4,9H,1-3H2,(H2,7,10)

Upstream product

• 85614-54-6 2-(2,4-dioxopyrrolidine-1-yl)acetamide 
• 10488-68-3 methyl 4-chloro-3-hydroxybutanoate 
• 598-41-4 H-Gly-NH₂ 
• 85614-53-5 methyl 2,4-dioxo-1-pyrrolidinacetate 
• 4509-09-5 Methyl (+/-)-3,4-epoxybutanoate 
• 1668-10-6 glycinamide hydrochloride 
• 62613-81-4 ethyl (4-hydroxy-2-oxopyrrolidin-1-yl)acetate 
• 114012-62-3 (1,5-dihydro-4-methoxy-2-oxo-2H-pyrrol-1-yl)acetamide 
• 174359-41-2 2-(4-Benzyloxy-2-oxo-pyrrolidin-1-yl)-acetamide 

Downstream Products

• 62833-66-3 2,5-Dihydro-2-oxo-1H-pyrrol-1-acetamid 
• 77191-37-8 4-hydroxy-2-oxo-1-pyrrolidine acetic acid 
• 1392812-96-2 C₆H₁₀N₂O₃*C₇H₆O₄ 
• 1392812-94-0 C₆H₁₀N₂O₃*C₇H₆O₅ 

Relevant articles and documents

Preparation method of 4-hydroxy-2-oxo-1-pyrrolidine acetamide

The invention belongs to the technical field of drug synthesis, in particular to a preparation method of 4-hydroxy-2-oxo-1-pyrrolidine acetamide. The 4-hydroxy-2-oxo-1-pyrrolidine acetamide is produced by intramolecular dehydration of 4-hydroxy-2-oxo-1-pyrrolidine acetic acid to obtain lactone which is then reacted with ammonia water. The preparation method of the 4-hydroxy-2-oxo-1-pyrrolidine acetamide has the advantages of short reaction period, mild conditions, low production cost, high product yield, good quality and the like, so that the method is suitable for industrial large-scale production.

A synthesis process of oxiracetam

The invention discloses a synthetic method for an anti-senile dementia drug of oxiracetam (I), and mainly provides a novel synthetic route. The method comprises the following steps of reacting a compound (when R is -Me and NO2) shown as a formula (V) with glycinamide hydrochloride of a compound shown as a formula (VI) under an alkaline condition to obtain a compound (wherein R is -Me and NO2) shown as a formula (IV); reacting the compound (wherein R is -Me and NO2) shown as the formula (IV) with ethyl 4-chloro-3-hydroxybutyrate of a compound shown as a formula (III) to obtain a compound (wherein R is -Me and NO2) shown as a formula (II); then removing protection groups under an acidic condition and intramolecularly cyclizing to obtain a compound shown as the formula (I) of 4-hydroxy-2-oxo-1-pyrrolidine acetamide, the compound (I) being oxiracetam. According to the synthetic route, raw materials and reagents have low toxicity, low cost and easy availability. The synthetic route is simple to operate, has relatively high yield and is suitable for industrial production.

Synthesis method of oxiracetam

The invention relates to a synthesis method of (S)-oxiracetam. The method comprises the following steps: (1) carrying out an esterification reaction on alcohol and S-4-amino-3-hydroxybutyrate taken as a starting material to obtain an intermediate I; (2) enabling the intermediate I and halogenated acetic ester to be subjected to a condensation reaction to obtain an intermediate II; (3) carrying out a ring closing reaction on the intermediate II to obtain an intermediate III; and (4) carrying out an ammonolysis reaction on the intermediate III to obtain the target product (S)-oxiracetam. After the synthesis route of the oxiracetam is adopted, the (S)-oxiracetam with more ideal yield of 20% or more is at least obtained; and therefore, a new oxiracetam synthesis route is opened up.