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Method for preparing taurine and substituted taurine

A technology of taurine and peracid, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of troublesome desalination and purification process, many steps, etc.

Inactive Publication Date: 2009-01-07
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] Although the above methods can be used to efficiently synthesize taurine and substituted taurine, some methods have more steps, or can only synthesize substituted taurine with certain structural types, or require troublesome desalination and purification processes

Method used

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  • Method for preparing taurine and substituted taurine

Examples

Experimental program
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Effect test

Embodiment 1

[0060] Preparation of taurine (2a)

[0061] 30% H 2 o 2 (12mL) and 88% HCO 2 H (120mL) was mixed and stirred at room temperature for 1h, and 2.38g (20mmol) of 1,3-thiazolidine-2-thione was added thereto under cooling in an ice-water bath, keeping the reaction temperature at 0-5°C. The reaction mixture was stirred and reacted Overnight, add performic acid again when the reaction is incomplete, evaporate the solvent after the completion of the reaction, and recrystallize the residue with ethanol to obtain 2.33 g of colorless crystal taurine, with a yield of 93% and a melting point of 325° C. (dec).

Embodiment 2

[0063] Preparation of (S)-2-aminopropylsulfonic acid (2b)

[0064] According to the method described in Example 1, using (S)-4-methyl-1,3-thiazolidine-2-thione as raw material to obtain (S)-2-aminopropylsulfonic acid, colorless crystals, melting point 317~319°C, yield 91%. [α] 20 D = -18.5(c, 1.11, H 2 O).

Embodiment 3

[0066] Preparation of (S)-3-methyl-2-amino-butylsulfonic acid (2c)

[0067] According to the method described in Example 1, using (S)-4-isopropyl-1,3-thiazolidine-2-thione as a raw material to obtain (S)-3-methyl-2-amino-butylsulfonate Acid, colorless crystal, melting point 325~326℃, yield 79%.[α] D 20 =+29.7 (c 1.01, HCO 2 H).

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Abstract

The invention provides a method for preparing taurine and substituted taurine, which takes 1, 3-thiazolidine-2-thioketone and derivants thereof as raw material to prepare taurine and substituted taurine. The method has the advantages that the raw material can be obtained easily, the operation is convenient, the purification through desalination is not needed, and the method is particularly suitable for large-scale industrialized production and can be utilized to prepare optically active substituted taurine. The obtained compound can be used as nutritive matters, medicines, enzyme inhibitors, antimicrobials, surface active agents, plant growth regulators, 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 taurine and substituted taurine. Background technique [0002] Taurine and substituted taurines are both a class of naturally occurring sulfur-containing amino acids (Timothy, C.; Birdsall, N.D. Alt. Med. Rev. 1998, 3, 128), and a class of natural protein amino acids with a tetrahedral structure. An important analogue of (Xu Jiaxi, Organic Chemistry, 2003, 23, 1). Taurine and substituted taurines are a class of small organic molecules with important biological functions (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 it is often used as an important nutrient and as a food additive. Taurine is beneficial to the growth and development of fetuses and infants, especially the differentiation and development of nerve cells and the enhanc...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14C07C303/16
Inventor 许家喜陈宁
Owner BEIJING UNIV OF CHEM TECH
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