Triethylamine → Levetiracetam

HRID 601727Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 601727
[CH2:1]([C@H:3]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[C:4](O)=[O:5])[CH3:2].C([N:15](CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[CH2:1]([C@H:3]([N:7]1[CH2:11][CH2:10][CH2:9][C:8]1=[O:12])[C:4]([NH2:15])=[O:5])[CH3:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 116079932-(2-Oxopyrrolidin-1-yl)butanoic acid, (2S)-

Produkt 1

HCID 5284583LevetiracetamAusbeute 81,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A suspension of (s)-alpha-ethyl-2-oxo-1-pyrrolidineacetic acid (45 g, 0.26 mol) in methylene chloride (225 ml) was cooled to 0° C. and triethylamine (53 g, 0.53 mol) and methanesulfonyl chloride (39 g, 0.34 mol) were added dropwise. The mixture was stirred at 0° C. for 30 min., then a stream of ammonia was purged in the solution for 2 hours. The insoluble solids were filtered and the filtrate was concentrated. The product was crystallized from methyl isobutyl ketone to give 36 g (80%) of (S)-alpha-ethyl-2-oxo-1-pyrrolidineacetamide.

Aufarbeitung

  1. customa stream of ammonia was purged in the solution for 2 hours
  2. filtrationThe insoluble solids were filtered
  3. concentrationthe filtrate was concentrated
  4. customThe product was crystallized from methyl isobutyl ketone

Quellen und Nachweise

ORD-Eintrag
ord-1f4ce74fbdcf4aa2b12baf610ca2733a
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902380B2

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