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Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same

A technology for tocopherol quinone and tocopherol, applied in the field of synthesizing the compound of formula I, can solve the problem of high concentration of by-products

Inactive Publication Date: 2013-01-16
EDISON PHARMA
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  • Abstract
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  • Application Information

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Problems solved by technology

[0007] However, conventional methods of synthesizing α-tocopherol often result in higher than desired concentrations of by-products

Method used

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  • Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same
  • Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same
  • Synthesis of alpha-tocopherolquinone derivatives, and methods of using the same

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Embodiment Construction

[0092] By charging an appropriate amount of R,R,R-α-tocopheryl acetate (7.0 kg) into a 72 L reaction vessel, α-tocopheryl acetate (Vita-Solar Biotechnology Co., China) was hydrolyzed to obtain the unisolated Intermediate of α-tocopherol. Dissolve α-tocopheryl acetate in ethanol (200 Proof denaturation with 0.05% toluene). The reaction vessel was cooled to 10-12°C and potassium hydroxide pellets (≥85% A.C.S. grade) were added to the flask while maintaining the temperature at 10-15°C. The mixture was stirred for 1 more hour. After at least 1 hour, the completion of the reaction was checked by sampling the batch and analyzing it by HPLC analysis.

[0093] The reaction is complete when the alpha-tocopheryl acetate is less than 0.5 area percent at 205 nm. The hydrolysis reaction product was neutralized with hydrochloric acid solution (34%-39% aqueous solution) in a reaction vessel to obtain α-tocopherol. The alpha-tocopherol solution was transferred to a 100 L separatory funnel...

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Abstract

The present invention is directed to a method of synthesizing a compound of Formula I: the method comprising oxidizing alpha-tocopherol with a metal salt oxidizing agent to form the compound of Formula I, wherein the stoichiometric ratio (mol / mol) of metal salt oxidizing agent / alpha-tocopherol is 1.6 to 4. The invention is also directed to a method of synthesizing a compound of Formula I, the method comprising (a) hydrolyzing alpha-tocopheryl acetate in the presence of a base; (b) neutralizing the hydrolyzing of (a), thereby forming alpha-tocopherol; and (c) oxidizing the alpha-tocopherol of I (b) with a metal salt oxidizing agent to form the compound of Formula I, wherein the stoichiometric ratio (mol / mol) of metal salt oxidizing agent / aipha-tocopherol is 1.6 to 4.

Description

technical field [0001] The present invention relates to the method for synthetic formula I compound: [0002] [0003] The method comprises oxidizing alpha-tocopherol with a metal salt oxidizing agent to form a compound of formula I, wherein the metal salt oxidizing agent / alpha-tocopherol stoichiometric ratio (mol / mol) is 1.6 to 4. The present invention also relates to a process for the synthesis of a compound of formula I comprising (a) hydrolyzing α-tocopheryl acetate in the presence of a base; (b) neutralizing the hydrolyzate of (a), thereby forming α-tocopherol and (c) oxidizing the alpha-tocopherol of (b) with a metal salt oxidizing agent, wherein the metal salt oxidizing agent / alpha-tocopherol stoichiometric ratio (mol / mol) is from 1.6 to 4 to form a compound of formula I. Background technique [0004] R,R,R-alpha-tocopherol is being developed for the treatment of conditions associated with mitochondrial disease. It occurs naturally in humans, but in very low conc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C46/06C07D311/72A61K9/00A61K31/125A61P25/00A61P9/00A61P13/12A61P27/02A61P3/10
CPCC07C46/06C07D311/72A61P11/00A61P13/02A61P13/12A61P15/08A61P25/00A61P25/02A61P25/08A61P25/14A61P25/16A61P25/18A61P25/28A61P27/02A61P3/00A61P35/00A61P9/00A61P3/10C07C50/28
Inventor S.D.佩斯利J.M.莱普利A.哈威M.埃克霍夫
Owner EDISON PHARMA
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