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Salt-free preparation method for substituted taurine

A technology of taurine and thiocarboxylic acid is applied in the field of salt-free preparation of taurine, and can solve problems such as troublesome desalination and purification processes

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

AI Technical Summary

Problems solved by technology

[0004] All of the above methods can be used to synthesize substituted taurine, but they all have a certain scope of application. Only certain structural types of substituted taurine can be synthesized, or a troublesome desalination purification process is required.

Method used

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Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0046] Preparation of 1-phenyl-2-aminoethanesulfonic acid (5a)

[0047] Dissolve 1-phenyl-2-nitroethylene (2.98g, 20mmol) in 20mL ether (or benzene, or THF), then add thioacetic acid (1.52g, 20mmol), and 200mg tributylamine, at room temperature Stir for 1h. After the reaction was completed, 20 mL of ether was added, followed by washing with 0.1 mol / L hydrochloric acid and deionized water respectively. The organic phase was dried, and the solvent was spun off. After recrystallization or column chromatography, 4.37 g of 1-phenyl-2-nitroethanethiol acetate was obtained, with a yield of 97%. It is a colorless crystal with a melting point of 126°C. 1 HNMR (300MHz, CDCl 3 )δ: 7.34~7.29(m, 5H, ArH), 5.29(t, J=7.5Hz, 1H, CHS), 4.84(d, J=7.5Hz, 2H, CHS 2 N), 2.36(s, 3H, CH3). 13 C NMR (75.5MHz, CDCl 3 )δ: 193.3, 135.6, 129.2, 128.8, 127.7, 77.9, 44.4, 30.3.

[0048] 30% LH 2 o 2 (10m) and 25mL of anhydrous formic acid were mixed and stirred in an ice-water bath for 0.5h. Then...

Embodiment 2

[0050] Preparation of 1-(4-chlorophenyl)-2-aminoethyl-1-sulfonic acid (5b)

[0051] According to the method described in Example 1, 1-(4-chlorophenyl)-2-aminoethyl-1-sulfonic acid was obtained from 1-phenyl-2-nitroethylene as a raw material, colorless crystals, melting point 342 ℃, 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.

Embodiment 3

[0053] Preparation of 3-methyl-1-aminobutane-2-sulfonic acid (5c)

[0054] According to the method described in Example 1, 3-methyl-1-aminobutane-2-sulfonic acid was obtained from 1-nitro-3-methyl-1-butene as a raw material, colorless crystals, melting point 338- 340°C, yield 64%. 1 H NMR (D 2 O, 300MHz) (δ, ppm) 0.89 (d, J=7.0Hz, 3H, CH 3 ), 0.97 (d, J=7.0Hz, 3H, CH 3 ), 2.22 (dqq, J=3.3, 7.0, 7.0Hz, 1H, CH), 2.87 (ddd, J=2.9, 3.3, 10.1Hz, 1H, CHS), 3.18 (dd, J=10.1, 13.8Hz, 1H in CH 2 N), 3.26 (dd, J=2.9, 13.8Hz, 1H in CH2N). 13 C NMR (D 2 O, 75.5MHz) (δ, ppm) 17.1, 21.1, 28.0, 37.4, 62.8.

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Abstract

The invention provides a salt-free preparation method for substituted taurine, and belongs to the technical field of organic synthesis. Nitroolefin and thionocarboxylic acid serving as raw materials are subjected to addition, oxidation and reduction to form the substituted taurine; and particularly, the method can be used for preparing cis and trans disubstituted and trisubstituted taurine. The preparation method has the advantages of simple and readily available raw materials, convenient operation and no troublesome desalting purification process, and suitability for large-scale industrial production. The compounds prepared by the method can be used as nutrient substances, medicaments, enzyme inhibitors, antibacterial agents, surfactants, plant growth regulators, raw materials for preparing sulfonamido peptide and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a salt-free preparation method of substituted taurine. Background technique [0002] Taurine and substituted taurine are a class of naturally occurring amino acids (Timothy, C.; Birdsall, N.D.Alt.Med.Rev.1998, 3, 128), a class of small organic molecules with important biological functions, Can affect calcium absorption and phosphorylation of proteins (Liebowitz, S.M.; Lombardini, J.B.; Salva, P.S. Biochem. Pharmac. 1988, 37, 1303). Taurine itself is one of the essential amino acids for the human body and is often used as an important nutrient and food additive. Taurine is beneficial to the growth and development of fetuses and infants, especially has a significant effect on enhancing the body's immunity. Taurine can also be used to prevent and treat colds, retinitis caused by lack of taurine, hypercholesterolemia, etc. Taurine and substituted taurine are ...

Claims

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Application Information

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IPC IPC(8): C07C303/22C07C303/02C07C309/24C07C309/14
Inventor 许家喜陈宁
Owner BEIJING UNIV OF CHEM TECH
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