Acetate → Maleate(2-)

HRID 1935318Notes

Reaction equation

HRID 1935318 reaction equation
[C:1]1(=[O:7])[O:6][C:4](=[O:5])[CH:3]=[CH:2]1.C(=O)([O-])[O-:9].C(=O)([O-])[O-].[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+].[C:24]([O-:27])(=[O:26])[CH3:25].[C:28]([O-:31])(=[O:30])[CH3:29].[Na+].C([O-])(=O)C.[K+]>O1CCCC1.C(#N)C.CC(C)=O>[C:1]([O-:6])(=[O:7])/[CH:2]=[CH:3]\[C:4]([O-:9])=[O:5].[C:28]([O-:31])(=[O:30])/[CH:29]=[CH:25]/[C:24]([O-:27])=[O:26]

Participants

12

Reactant 7

HCID 175AcetateHCID 7923Maleic AnhydrideHCID 10340Sodium CarbonateHCID 11430Potassium CarbonateHCID 19660Carbonate IonHCID 517044Potassium AcetateHCID 517045Sodium Acetate

Product 2

HCID 5288227Maleate(2-)HCID 5460307Fumarate

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

Specifically, the procedure is as follows. First, vitamin E (II) is reacted with maleic anhydride (III) in the presence of an alkaline carbonate (sodium carbonate, potassium carbonate or the like) or an alkaline acetate (sodium acetate, potassium acetate or the like) in a nonpolar solvent such as acetone, acetonitrile or tetrahydrofuran (THF) for about 1 to 3 hours while heating to give mono-tocopheryl maleate (or fumarate) (IV) (which is a novel compound not found in publications so far). The compound (IV) thus produced may further be subjected to a condensation reaction with an amino acid (glycine, β-alanine, γ-aminobutyric acid, 5-aminovaleric acid, ε-aminocaproic acid, anthranilic acid, tranexamic acid, proline, one of their esters, aminoethylsulfonic acid, or aminoethylsulfinic acid) or an amine (serotonin) in a solvent such as chloroform or tetrahydrofuran in the presence of an organic amine (pyridine, triethylamine or the like) according to the mixed anhydride method using ethyl chloroformate or the like to give a corresponding acid amide (V) of mono-tocopheryl maleate (or fumarate) (IV). The compound (IV) or (V) then is subjected to an addition reaction with an SH compound (glutathione, γ-glutamylcysteine, cysteine, penicillamine, an ester thereof, or cysteamine), a component of the present compound, at room temperature for about 3 to 6 hours and then about 1 to 3 hours while warming to give the present compound (I). A reaction solvent for this may be water or a solvent miscible with water, e.g., alcohol, acetonitrile or dioxane, which preferably is used as a mixture with water.

Sources & evidence

ORD record
ord-fe554f279c80417687bdaf7dca621fd9
Source dataset
uspto-grants-2002_05
Patent number
US06387882B1

Reaction notes

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