Diethyl Ether → 3-Ethoxypropionyl carnitine perchlorate

HRID 280582

Reaktionsgleichung

Reaktionsgleichung von HRID 280582
[Cl:1]([O:5][CH:6]([CH2:12][C:13](=[O:15])[O-:14])[CH2:7][N+:8]([CH3:11])([CH3:10])[CH3:9])(=[O:4])(=[O:3])=[O:2].[CH2:16]([O:18][CH2:19][CH2:20][C:21](Cl)=[O:22])[CH3:17].C(Cl)(Cl)Cl.CO.O.[NH4+].[OH-].C(OCC)C>CC#N.CC(C)=O>[Cl:1]([O:5][C:6]([C:21](=[O:22])[CH2:20][CH2:19][O:18][CH2:16][CH3:17])([CH2:12][C:13](=[O:14])[O-:15])[CH2:7][N+:8]([CH3:11])([CH3:9])[CH3:10])(=[O:2])(=[O:4])=[O:3]

Komponenten

7

Edukt 4

HCID 3283Diethyl EtherHCID 124253413-Ethoxypropanoyl chlorideHCID 19426511chloroform methanol water NH4OHHCID 20140201Carnitine perchlorate

Produkt 1

HCID 1317146813-Ethoxypropionyl carnitine perchlorate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

3.9 g (0.015 moles) of carnitine perchlorate were dissolved in 50 cc of anhydrous CH3CN. To this solution 3-ethoxypropionyl chloride was added dropwise with a dropping funnel while cooling to about 0° C. with an ice bath. The reaction mixture was allowed to stand for 48 hours at room temperature (TLC chloroform-methanol-water-NH4OH 55:35:5:5). During this period of time a stream of nitrogen was blown into the reaction mixture at intervals of about 5 minutes, in order to remove the hydrochloric acid formed during the reaction. The reaction mixture was slowly poured into 300 cc of ethyl ether. A precipitate was thus obtained which was taken up with anhydrous acetone and the resulting solution was allowed to stand for some hours. The solution was filtered and ethyl ether was added thereto and a precipitate formed. The precipitate dried under vacuum presented the appearence of a transparent and viscous oil which consisted of 3-ethoxypropionyl carnitine perchlorate.

Aufarbeitung

  1. waitDuring this period of time a stream of nitrogen was blown into the reaction mixture at intervals of about 5 minutes, in order
  2. customto remove the hydrochloric acid
  3. customformed during the reaction
  4. customA precipitate was thus obtained which
  5. waitto stand for some hours
  6. filtrationThe solution was filtered
  7. additionethyl ether was added
  8. customa precipitate formed
  9. customThe precipitate dried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-47884e8a22f34b9fb8eefc91c2b7604a
Quelldatensatz
uspto-grants-1986_05
Patentnummer
US04590209

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