Potassium Hydroxide → Levetiracetam

HRID 492225Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 492225
Cl.[NH2:2][C@@H:3]([CH2:7][CH3:8])[C:4]([NH2:6])=[O:5].[OH-].[K+].Cl[CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16]>ClCCl.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH2:7]([C@H:3]([N:2]1[CH2:12][CH2:13][CH2:14][C:15]1=[O:16])[C:4]([NH2:6])=[O:5])[CH3:8]

Komponenten

6

Edukt 3

HCID 14797Potassium HydroxideHCID 783704-Chlorobutyryl chlorideHCID 11961924(2S)-2-Aminobutanamide hydrochloride

Produkt 1

HCID 5284583LevetiracetamAusbeute 60 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

The compound (−)-(S)-α-ethyl-2-oxo-1-pyrrolidineacetamide is prepared by suspending 50 grams of (S)-2-aminobutyramide hydrochloride in 500 mL of dichloromethane at room temperature, then cooling to temperatures between −5 and 0° C. and adding 81.2 grams of potassium hydroxide and 23.3 grams of tetrabutylammonium bromide at those temperatures. A 66.4 gram amount of 4-chlorobutyryl chloride is added at the same temperatures. After completion of the reaction, solids are removed by filtration, the solution is adjusted to pH 7-7.5 with acetic acid, and dichloromethane is partially evaporated by the application of a vacuum. 150 mL of ethyl acetate are added to precipitate the product, which is isolated by filtration and washed with ethyl acetate and then with acetone; the product has a chiral purity of 99.8 percent by high performance liquid chromatography. The final product is purified by recrystallization from ethyl acetate, giving a yield of 60-65 percent.

Aufarbeitung

  1. customat room temperature
  2. temperaturecooling to temperatures between −5 and 0° C.
  3. customAfter completion of the reaction, solids
  4. customare removed by filtration
  5. customis partially evaporated by the application of a vacuum
  6. addition150 mL of ethyl acetate are added
  7. customto precipitate the product
  8. customwhich is isolated by filtration
  9. washwashed with ethyl acetate
  10. customThe final product is purified by recrystallization from ethyl acetate
  11. customgiving a yield of 60-65 percent

Quellen und Nachweise

ORD-Eintrag
ord-c724c900e6574659844ddd9cc0985927
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531673B2

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