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Preparation method of 1-substituted taurine

A technology of taurine and xanthate, applied in the field of preparation of 1-position substituted taurine, can solve the problems of troublesome desalination and purification process, many steps and the like

Active Publication Date: 2010-10-06
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0004] All of the above methods can be used to effectively synthesize 1-substituted taurine, but some methods have more steps, or require troublesome desalination purification process

Method used

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  • Preparation method of 1-substituted taurine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0043] Preparation of 1-phenyl-2-aminoethylsulfonic acid (3a)

[0044] Dissolve 5.42 g (20 mmol) of O-ethyl dithiocarbonate S-(1-phenyl-2-nitroethyl) ester in formic acid (12 mL), and add H 2 o 2 (2.4mL), keep the reaction temperature at 0-5°C and stir the reaction overnight. After the reaction is completed, the solvent is distilled off to obtain 1-phenyl-2-nitroethylsulfonic acid.

[0045] Dissolve the obtained 1-phenyl-2-nitroethylsulfonic acid in methanol, add 60 mg of 10% palladium carbon, reduce it with hydrogen under stirring, evaporate the solvent, and recrystallize with ethanol to obtain colorless crystal 1- Phenyl taurine 2.33g, yield 58%, melting point 352°C (dec). 1 H NMR (D 2 O, 200MHz) (δ, ppm): 3.54 (dd, J=8.4, 13.3Hz, 1H in CH 2 N), 3.76(dd, J=6.8, 13.3Hz, 1H in CH 2 N), 4.27(dd, J=6.8, 8.4Hz, 1H, CHS), 7.38(s, 5H, ArH). 13 C NMR (DMSO-d 6 , 50MHz) (δ, ppm): 40.9, 61.5, 127.2, 127.9, 129.0, 136.1.

Embodiment 2

[0047] Preparation of 1-(4-methylphenyl)-2-aminoethylsulfonic acid (3b)

[0048] According to the method described in Example 1, use O-ethyl dithiocarbonate S-[1-(4-methylphenyl)-2-nitroethyl] ester as raw material to obtain 1-(4-methyl Phenyl)-2-aminoethylsulfonic acid, colorless crystals, melting point 339-342°C, yield 60%. 1 H NMR (D 2 O, 300MHz) (δ, ppm) 2.24 (s, 3H, CH 3 ), 3.49 (dd, J=8.4, 13.3Hz, 1H in CH 2 N), 3.71(dd, J=6.8, 13.3Hz, 1H in CH 2 N), 4.21 (dd, J=6.8, 8.4Hz, 1H, CHS), 7.19 (d, J=8.4Hz, 2H, ArH), 7.24 (d, J=8.4Hz, 2H, ArH). 13 C NMR (D 2 O, 75.5MHz) (δ, ppm) 20.9, 40.8, 63.1, 129.5, 129.6, 130.3, 140.3.

Embodiment 3

[0050] Preparation of 1-(4-chlorophenyl)-2-aminoethyl-1-sulfonic acid (3c)

[0051] According to the method described in Example 1, use dithiocarbonic acid O-ethyl ester S-[1-(4-chlorophenyl)-2-nitroethyl] ester as raw material to obtain 1-(4-chlorophenyl )-2-aminoethylsulfonic acid, colorless crystals, melting point 342°C, yield 67%. 1 H NMR (D 2 O, 300MHz) (δ, ppm) 3.47 (dd, J=8.7, 13.4Hz, 1H in CH 2 N), 3.76(dd, J=6.9, 13.4Hz, 1H in CH 2 N), 4.27 (dd, J=6.9, 8.4Hz, 1H, CHS), 7.38 (m, 4H, ArH). 13 C NMR (D 2 O, 75.5MHz) (δ, ppm) 41.1, 61.9, 129.2, 129.4, 130.9, 134.9.

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Abstract

The invention provides a preparation method of 1-substituted taurine, and belongs to the technical field of organic synthesis. Nitro alkyl xanthate is taken as a raw material to be oxidized and reduced to obtain substituted taurine. The preparation method has simple raw materials and easy obtainment of raw materials, and convenient operation, does not need tedious desalination and purification process, is suitable for large-scale industrial production, and can be used for optical activity to substitute the preparation of taurine. The obtained compound can be used as nutrients, drugs, enzyme inhibitors, antibacterial agents, surfactants, plant growth regulators, raw materials for preparing sulfonyl peptides and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 1-position substituted taurine. Background technique [0002] Taurine and substituted taurines are a class of naturally occurring amino sulfonic acids (Timothy, C.; Birdsall, N.D. Alt. Med. Rev. 1998, 3, 128), and an important class of natural protein amino acids with tetrahedral Sulfur-containing analogs of the structure (Xu Jiaxi, Organic Chemistry, 2003, 23, 1). They are a class of small organic molecules with important biological functions, affecting calcium absorption and protein phosphorylation (Liebowitz, S.M.; Lombardini, J.B.; Salva, P.S. Biochem. Pharmac. 1988, 37, 1303). Taurine is one of the essential amino acids for the human body and is often used as an important nutrient and food additive. Taurine can also be used to prevent and treat colds, neuralgia, drug poisoning, retinitis and hypercholesterolemia caused by lack ...

Claims

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Application Information

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IPC IPC(8): C07C303/22C07C303/02C07C309/24C07C309/19C07C309/14
Inventor 许家喜徐传祥
Owner BEIJING UNIV OF CHEM TECH