DL-Carnitine → (-)-Carnitine

HRID 64793

Reaktionsgleichung

Reaktionsgleichung von HRID 64793
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].C([C@@](C(O)=O)(O)[C@@](C(=O)C1C=CC=CC=1)(O)C(O)=O)(=O)C1C=CC=CC=1>CO>[OH:11][C@@H:6]([CH2:7][C:8](=[O:9])[O-:10])[CH2:5][N+:2]([CH3:4])([CH3:1])[CH3:3].[OH:11][C@H:6]([CH2:7][C:8](=[O:9])[O-:10])[CH2:5][N+:2]([CH3:4])([CH3:1])[CH3:3]

Komponenten

5

Edukt 2

HCID 288DL-CarnitineHCID 12362976dibenzoyl-L(+)tartaric acid

Produkt 2

HCID 10917(-)-CarnitineHCID 2724480D-Carnitine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

In 700 ml of methanol are dissolved under heat 35.0 g (0.177 mole) of DL-carnitine hydrochloride, and the solution is passed through OH type strongly basic resin (DOWEX-1X8). The methanol solution is concentrated to obtain 28.3 g (0.175 mole) of DL-carnitine. To DL-carnitine are added 62.6 g (0.175 mole) of dibenzoyl-L(+)tartaric acid and 93 ml of methanol, and the mixture is dissolved under heat to form dibenzoyl-L( +)tartarates of D-carnitine and L-carnitine. The tartarates are cooled at a temperature of below -10° C. with stirring to fractionally crystallize L-carnitine dibenzoyl-L(+)tartarate. The tartarare is filtered and washed to give L-carnitine dibenzoyl-L(+)tartarate (yield 30.5 g, purity 93.0%). Recrystallization of the tartarate from 100 ml of methanol gives 23.9 g of L-carnitine dibenzoyl-L(+)tartarate as white crystal. [α]D25 =-96.0° (c=1, MeOH), m.p. 154° C. (dec.), purity 99.5%.

Aufarbeitung

  1. dissolutionthe mixture is dissolved
  2. temperatureunder heat

Quellen und Nachweise

ORD-Eintrag
ord-85a1e07aaddb48bb9567fe3c06557f05
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04610828

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