Title:
MANUFACTURE OF L-(-)-CARNITINE FROM WASTE-PRODUCT HAVING OPPOSITE CONFIGURATION
Document Type and Number:
Japanese Patent JP3502649
Kind Code:
B2
Abstract:
PURPOSE: To manufacture L-(-)-carnitine useful as pharmaceuticals, in high yield without need of conversion of the waste-product into an achiral intermediate, from a (D)-(+)-carnitine derivative.
CONSTITUTION: This compound is manufactured by hydrolyzing a salt of (D)-(+)- carnitine of formula I (X- is a counter ion) to obtain (D)-(+)-carnitine of formula II, then esterifying the resulting compound to obtain a compound of formula III (R1 is a 1-11C alkoxy or (di)arylalkoxy), reacting the ester of formula III with an acylating agent of the formula RY (Y is a halogen, RY is anhydride) in the presence of an organic base at 0-50°C to obtain an acyl-derivative of formula IV (Y- is a counter ion or an OR-leaving group; R is a 1-12C alkylsulfonyl or the like), further, after obtaining acyl-(D)-(+)-carnitine of formula V by converting COR1 group of the compound of formula IV into carboxyl group, lactonizing the compound of formula V in a basic medium to obtain a lactone of L-(-)-carnitine of formula VI, converting the lactone into L-(-)- carnitine and finally isolating an inner salt of L-(-)-carnitine.
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Inventors:
Fabio Janessi
Maria Laura Bolognesi
Maria Ornella Chinch
Francesco de Angelis
Maria Laura Bolognesi
Maria Ornella Chinch
Francesco de Angelis
Application Number:
JP31979293A
Publication Date:
March 02, 2004
Filing Date:
December 20, 1993
Export Citation:
Assignee:
SIGMA-TAU INDUSTRIE FARMACEUTICHE RIUNITE SOCIETA PER AZIONI
International Classes:
C07C227/32; C07C229/22; C07D305/12; C07C227/30; (IPC1-7): C07C227/30; C07C229/22; C07D305/12
Domestic Patent References:
| JP54113409A | ||||
| JP59231048A |
Other References:
【文献】米国特許3830931(US,A)
Attorney, Agent or Firm:
Aoyama Ryo (2 outside people)