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(S) or (R)-6-hydroxyl-8-alkoxide octylic acid, its ester, salt, amide, preparation method and application thereof

A technology of alkoxyl and its amide, which is applied in the field of synthesis or -lipoic acid, and can solve the problems of expensive raw materials

Inactive Publication Date: 2011-04-20
SHANGHAI INST OF PHARMA IND CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

The raw materials of this method are relatively expensive, and the alkylation reaction needs to be completed under anhydrous, anaerobic, and low temperature conditions.

Method used

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  • (S) or (R)-6-hydroxyl-8-alkoxide octylic acid, its ester, salt, amide, preparation method and application thereof
  • (S) or (R)-6-hydroxyl-8-alkoxide octylic acid, its ester, salt, amide, preparation method and application thereof
  • (S) or (R)-6-hydroxyl-8-alkoxide octylic acid, its ester, salt, amide, preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1～17

[0054] Embodiment 1~17 (S) or (R)-6-hydroxyl-8-alkoxy octanoic acid and its ester

[0055] Table 1 shows examples 1 to 17 of the compound (S) or (R)-6-hydroxy-8-alkoxy octanoic acid and its esters with the structural formula shown in formula I.

[0056] Formula I

[0057] Table 1 (S) or (R)-6-hydroxyl-8-alkoxy octanoic acid and its esters Examples 1-17

[0058] Example

[0059] 11

Embodiment 18～22

[0060] Embodiment 18~22 (S) or (R)-6-hydroxyl-8-alkoxy octanoate

[0061] Table 2 shows examples 18-22 of the compound (S) or (R)-6-hydroxy-8-alkoxy octanoate with the structural formula shown in formula II.

[0062] Formula II

[0063] Table 2 (S) or (R)-6-hydroxyl-8-alkoxy octanoate embodiment 18~22

[0064] Example

Embodiment 23～27

[0065] Embodiment 23~27 (S) or (R)-6-hydroxyl-8-alkoxy octanamide

[0066] Table 3 shows examples 23-27 of the compound (S) or (R)-6-hydroxyl-8-alkoxyoctylamide having the structural formula shown in formula III.

[0067] Formula III

[0068] Table 3 (S) or (R)-6-hydroxyl-8-alkoxy octanamide embodiment 23~27

[0069] Example

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Abstract

The invention discloses a novel compound (S) or (R)-6-hydroxy-8-alcoxide octoic acid and an ester thereof represented as formula I, a salt thereof represented as formula II and an amide thereof represented as formula III, wherein R1 is C1-C4 alkyl or phenylmethyl-CH2Ph, phenylethyl-C2H4Ph, R2 is H, C1-C12 alkyl or aralkyl, C5-C7 cycloalkyl or C6-C10 aromatic radical. When R2 is CH3, R1 isn't CH3; X=Y=1 or 2 and M is alkali metal or alkali earth metal. The invention also discloses a preparation method and application as an important reaction intermediate for synthesizing (S) or (R)-lipoicin or (S) or (R)-thioctamide.

Description

technical field [0001] The present invention relates to a class of novel compound (S) or (R)-6-hydroxyl-8-alkoxy octanoic acid and its ester, its salt and its amide, as well as the preparation method of this type of compound and as a reaction intermediate in the synthesis (R) or (S)-lipoic acid, or (R) or (S)-lipoamide for use. Background technique [0002] Bezbarua etc. [Bezbarua.M.S, Synthesis, 11,1289 (1996)] stereoselectively reduce the carbonyl in 6-oxo-8-alkoxy octanoate by biological method, thereby make (S)-6-hydroxy - Methyl 8-methoxyoctanoate. This method bioreduction space-time yield is low, and the preparation [Shojiro Y., Mitsuo N., Yakugaku Zasshi, 80,1170(1960) of used raw material 6-oxo-8-alkoxy octanoate; Bezbarua M.S, Synthesis , 11, 1289(1996)] is more complicated. [0003] Reports such as Liu [Liu C., Coward J.K., J.Med.Chem., 34, 2094 (1991)] obtain chiral cyclohexanone derivatives by asymmetric alkylation, and then obtain similar formula IV by Baeyer...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C59/125C07C59/13C07C69/712C07C69/708C07C235/34C07C231/02C07D339/04
Inventor 刘娜黄成军周后元
Owner SHANGHAI INST OF PHARMA IND CO LTD