Preparation method of 1-substituted homotaurine

A technology of high taurine and taurine, applied in the preparation of sulfonic acid, organic chemistry, etc., can solve the problems of troublesome desalination and purification process, limited scope of application, etc.

Inactive Publication Date: 2012-04-25
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] Existing these methods all can be used for synthesizing homotaurine or derivatives thereof, but often the scope of application is limited, can only synthesize the substituting homotaurine of certain structure type, or need troublesome desalination purification process, the most important The problem is that it is not easy to introduce a variety of functional groups at the 1-position of homotaurine

Method used

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  • Preparation method of 1-substituted homotaurine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] 1-phthalimido-3-nonylsulfonic acid 3a preparation of

[0056] Add dithiocarbonic acid- O -Ethyl- S - Phthalimide methyl ester (xanthate) (562 mg, 2 mmol), evacuated, N 2 A solution of n-octene (448 mg, 4 mmol) in 1 mL of 1,2-dichloroethane (DCE) was added under protection, and 21 mg of lauroyl peroxide (DLP) ( 2.5 mol%), the reaction was detected by TLC, and DLP (1.25-10 mol%) was added every 45 min until the reaction of the raw material xanthate was complete, and the reaction was stopped. The solvent was removed from the reaction solution by silica gel column separation to obtain the addition product shown in Formula 2.

[0057] Add the above addition product (353 mg 1 mmol) into a 25 mL round bottom flask, add 1 mL THF to dissolve, add 5 mL anhydrous formic acid, place in an ice-water bath for 10 min, slowly add 30% H 2 o 2 (1 mL), the reaction was stirred overnight. Spin off the solvent and separate on a silica gel column (eluent petroleum ether: ethyl ac...

Embodiment 2

[0059] 1-phthalimido-3-heptanesulfonic acid 3b preparation of

[0060] According to the method described in Example 1, with dithiocarbonic acid- O -Ethyl- S - Phthalimidomethyl ester and n-hexene were used as raw materials to obtain 1-phthalimido-3-heptanesulfonic acid as a brown oily liquid with a yield of 57%. 1 H NMR (D 2 o , 400MHz) d ppm: 0.63 (t, J = 7.0 Hz, 3H, CH 3 ), 1.03-1.26 (m, 4H, 2CH 2 ), 1.34-1.42 (m, 1H in CH 2 ), 1.62-1.72 (m, 2H in 2CH 2 ), 1.91 (dddd, J = 13.1, 6.6, 6.5, 6.3 Hz, 1H in NCH 2 ), 2.53-2.58 (m, 1H, SCH), 3.52 (t, J = 7.1 Hz, 2H, NCH 2 ), 7.50-7.57 (m, 4H, ArH). 13 C NMR (D 2 o , 100MHz) d ppm: 13.1, 21.9, 28.0, 29.0, 28.3, 35.9, 57.8, 123.2, 130.9, 134.7, 170.0.

Embodiment 3

[0062] 1-Cyclohexyl-4-phthalimido-2-butanesulfonic acid 3c preparation of

[0063] According to the method described in Example 1, with dithiocarbonic acid- O -Ethyl- S - Phthalimide methyl ester and 3-cyclohexyl-1-propene as raw materials to obtain 1-cyclohexyl-4-phthalimido-2-butanesulfonic acid, pale yellow oily liquid , yield 73%. 1 H NMR (D 2 o , 400MHz) d ppm: 0.50-1.48 (m, 13H, CH 2 & H in cyclohexyl), 1.69 (s, 1H in CH 2 ), 1.90 (s, 1H CH 2 ), 2.63 (s, 1H, SCH), 3.56 (s, 1H, 1H in NCH 2 ), 3.61 (s, 1H in NCH 2 ), 7.58 (s, 4H, ArH). 13 C NMR (D 2 o , 100MHz) d ppm: 25.6, 25.9, 26.0, 28.6, 31.8, 33.6, 34.5, 36.3, 37.3, 55.2, 123.2, 132.0, 134.7, 169.9, 214.2.

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Abstract

The invention provides a preparation method of N-phthaloyl protected 1-substituted homotaurine. The method comprises: conducting free radical addition to terminal olefin by dithiocarbonic acid-O-alkyl-S-phthalimidemethyl ester so as to obtain corresponding xanthate, then carrying out oxidation to prepare N-phthaloyl protected 1-substituted homotaurine, then performing acid or base catalyzed hydrolysis or hydrazinolysis, thus obtaining 1-substituted homotaurine. The preparation method of the invention has simple and easily available raw materials, convenient operation, and no need for a tedious desalting and purifying process, thus being especially suitable for large scale industrial production. And the prepared compound can be use as a nutrient, a medicament, an enzyme inhibitor, an antimicrobial agent, a surfactant, a plant growth regulator, and a raw material for preparing sulfono-peptides, etc.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 1-substituted homotaurine. Background technique [0002] Homotaurine, that is, γ-aminopropanesulfonic acid, is an aminoalkylsulfonic acid isolated from Centipede lingulae. Because of its structure similar to neurotransmitter γ-aminobutyric acid, it has been found through research Anticonvulsant effects of gamma-aminobutyric acid (Fariello, R. G.; Golden, G. T.; Pisa, M. Neurology 1982, 32 , 241). High taurine is also the only nitrogen source for certain in vivo metabolism, which can prevent and treat sclerosis of the conjunctival sheath, prevent hair loss, treat alcohol dependence, inhibit the oxidation of catecholamines in the body, protect DNA from oxidative damage, improve memory, strengthen the heart, Lower blood pressure and other effects (Mayer, J.; Cook, A. M. J. Bacteriol . 2009, 191 , 6052; Rouhani, S.; Dallava Santucc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D209/48C07C309/14C07C303/22
Inventor 许家喜黄忠衍
Owner BEIJING UNIV OF CHEM TECH
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