Process for producing L-carnitine from D,L-carnitine nitrile sal

Details Process for producing L-carnitine from D,L-carnitine nitrile sal Process for producing L-carnitine from D,L-carnitine nitrile sal

1992-03-27

1992-11-24

Shippen, Michael L.

Organic compounds -- part of the class 532-570 series

Organic compounds

Carboxylic acids and salts thereof

548535, C07C22900

Patent

active

051664267

ABSTRACT:
Synthesis of L-carnitine by chemical optical resolution of D,L-carnitine nitrile salts, where the D,L-carnitine nitrile salt is reacted with optically active N-acetylproline as the resolving agent in order to form the diastereomer salts after conversion to the hydroxide form, one of the two diastereomer salts is separated by fractional crystallization and the fraction containing mainly L-carnitine nitrile salt is treated with an optically inactive strong acid in order to split off the optically active N-acetylproline and then the resolving agent is separated and the resulting L-carnitine nitrile salt is saponified to L-carnitine. N-acetyl-L-proline is used as the resolving agent and the diastereomer (LL) salt is obtained in crystalline form in a high optical purity by fractional crystallization and the L-carnitine nitrile salt obtained after splitting off and separating N-acetyl-L-proline is used directly for saponification without further crystallization.

REFERENCES:
patent: 3488729 (1970-01-01), Jakob et al.
patent: 4914208 (1990-04-01), Jakob et al.
An English language abstract of JP 62-286969 (including Chemical Abstract 109: 73908f) Jun. 6, 1989.
Strack, E., et al., "Die Darstellung von L-Carnitin und seiner Isomeren", Z. physiol. Chem. (1960), vol. 318, pp. 129-137, vol. 51, pp. 283-290.

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