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US 5,491,260 AGranted
Process for manufacturing L-(-)-carnitine from derivatives having a configuration opposite to that of L-(-)-carnitine
AssigneeSigma-Tau Industrie Farmaceutiche Riunite S.p.A.
InventorsFabio Giannessi, Roberto Castagnani, Maria O. Tinti, Francesco De Angelis, Paolo De Witt, Domenico Misiti
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Abstract
A Process for Preparing L-(-)-carnitine is disclosed which comprises acylating D-(+)-carnitinenitrile or D-(+)-carnitineamide to their respective acyl derivatives which, via acid hydrolysis, yield D-(+)-carnitine which is converted to the lactone of L-(-)-carnitine. The lactone when in base yields L-(-)-carnitine.
Claims19
A process for producing L-(-)-carnitine from D-(+)-carnitinenitrile 1 and D-(+)-carnitineamide 1' having the formulas 1 and 1' ##STR3## wherein X.sup.- is a counterion, which comprises:
- (a) converting 1 or 1' to acyl D-(+)-carnitinenitrile 2 or acyl D-(+)-carnitineamide 3 having the formulas ##STR4## wherein R is selected from the group consisting of C.sub.1 -C.sub.12 alkylsulfonyl, formyl, trifluoroacetyl, p-toluenesulfonyl, p-bromobenzenesulfonyl, trifluoromethanesulfonyl, nonafluorobutanesulfonyl, 2,2,2-trifluoroethanesulfonyl, and p-nitrobenzenesulfonyl radicals;
- (b) converting the acyl D-(+)-carnitinenitrile 2 or the acyl D-(+)-carnitineamide 3 via acid hydrolysis to acyl D-(+)-carnitine 4 of the formula ##STR5## (c) lactonizing the acyl D-(+)-carnitine 4 to the lactone of L-(-)-carnitine 5 of the formula ##STR6## by treating 4 with base;
- and (d) converting the lactone 5 to L-(-)-carnitine by treating 5 with base.
Dependencies are inferred from the claim text.