Title:
PRODUCTION OF SHIKIMIC ACID AND ITS DERIVATIVE
Document Type and Number:
Japanese Patent JP3641384
Kind Code:
B2
Abstract:
PROBLEM TO BE SOLVED: To obtain shikimic acid and its derivative useful as an intermediate for synthesizing a pharmaceutically active compound while attaining high selectivity in the dehydrated position by dehydrating quinic acid by means of Vilsmeier reagent.
SOLUTION: Shikimic acid and its derivative are obtained by dehydrating quinic acid and its derivative, pref. a compound of the formula (R1 is H or a carboxylic acid-protecting group; R2-R4 are each H, a hydroxy-protecting group, or the like) or its salt (pref. ethyl 3,4-isopropylidene-5-mesyl-quinate) by means of Vilsmeier reagent pref. in ethyl acetate at 50-80°C. Vilsmeier reagent is pref. prepared in situ by means of POCl3, oxalyl dichloride or phosgene each in dimethylformamide(DMF), where the solution of quinic acid in DMF is reacted with excess (pref. 1.1-1.5 equivalents) POCl3, oxalyl dichloride or phosgene at room temperature for 1 h.
More Like This:
Inventors:
Hans-Jurgen Maia
Application Number:
JP12792099A
Publication Date:
April 20, 2005
Filing Date:
May 10, 1999
Export Citation:
Assignee:
F. HOFFMANN-LA ROCHE AKTIENGESELLSCHAFT
International Classes:
C07C51/377; C07D317/68; C07C62/32; C07C62/34; C07C67/327; C07C69/757; C07C303/30; C07C309/66; (IPC1-7): C07D317/68
Domestic Patent References:
| JP1121267A |
Attorney, Agent or Firm:
Hajime Tsukuni
Fumio Shinoda
Fumio Shinoda