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Preparation of taurine and derivatives thereof

A kind of derivative, the technology of taurine, applied in the field of preparation of taurine and derivatives thereof, can solve the problems such as unfavorable industrial production, complicated operation and handling

Inactive Publication Date: 2008-09-03
PEKING UNIV
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In the above-mentioned methods, most of them use inorganic salts. In order to obtain high-purity products, purification processes such as desalination must be repeated, which requires complicated operations and treatments, which is not conducive to large-scale industrial production.

Method used

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  • Preparation of taurine and derivatives thereof
  • Preparation of taurine and derivatives thereof
  • Preparation of taurine and derivatives thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0058] Preparation of N-acetyltaurine and taurine (1a)

[0059] (1) Open loop:

[0060] Add 1.332g (31mmol) aziridine, 5.89g (77.4mmol) thioacetic acid and 150mL tetrahydrofuran into a 250mL three-necked flask, stir at reflux for 8h, spin off the solvent to obtain an oily product.

[0061] (2) Oxidation:

[0062] The oil obtained above was dissolved in 88% HCO 2 H (27 mL). 30% H 2 o 2 (45mL) and 88% HCO 2 H (150 mL) was mixed and stirred at room temperature for 1 h, and added dropwise to the above solution under cooling in an ice-water bath, keeping the reaction temperature at 0-5°C. The reaction mixture was brought to room temperature and stirred for one day. The solvent was distilled off to obtain the solid product N-acetyltaurine, and the total yield of the two steps was 98%.

[0063] (3) Hydrolysis:

[0064] The above solid product was dissolved in 10% hydrochloric acid and refluxed overnight. The solvent was evaporated, and the residue was washed with ethanol to...

Embodiment 2

[0066] Preparation of (S)-3-methyl-2-acetylamino-butylsulfonic acid and (S)-3-methyl 2-amino-butylsulfonic acid (1b)

[0067] According to the method described in Example 1, (S)-2-isopropylaziridine was used as a raw material to obtain (S)-3-methyl-2-acetylamino-butylsulfonic acid, colorless crystals, two The total yield in one step is 65%; its hydrolysis gives (S)-3-methyl-2-amino-butylsulfonic acid as colorless crystals, the melting point is 326-329°C, and the total yield in three steps is 61%.

Embodiment 3

[0069] Preparation of (S)-3-methyl 2-amino-butylsulfonic acid (1b)

[0070] According to the method described in Example 1, ring-opening with thioacetic acid in benzene, using (S)-2-isopropylaziridine as a raw material to obtain (S)-3-methyl-2-amino-butyl Sulfuric acid, colorless crystals, melting point 326-329°C, the total yield of three steps is 70%. 13 C NMR (75.5MHz, HCO 2 H)δ: 16.2, 17.1, 30.3, 49.3, 54.6.

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Abstract

The invention provides a novel preparation method for taurine, substituted taurine and N-acylated derivates. The method comprises taking aziridine and substituted aziridine as raw material, obtaining N-acylated taurine derivates by opening loop and oxygenizing, hydrolyzing N-acylated taurine derivates to obtain taurine or substituted taurine. The raw material of the preparation method is simple and easy to get and prepare, especially convenient to separate and purify, and can be used for the preparation of optical activity substituted taurine and N-acyl group substituted taurine. The obtained compounds can be used as nutrient substance, medicament, enzyme inhibitors, antibacterial agents, surface active agents, plant growth regulators and raw materials for preparing sulfonopeptides.

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 its derivatives. Background technique [0002] Sulfamic acid is not only a class of naturally occurring amino acids (Timothy, C.; Birdsall, N.D.Alt.Med.Rev.1998, 3, 128), but also an important analogue of a class of natural amino acids with a tetrahedral structure (Xu Jiaxi, organic Chemistry, 2003, 23, 1). Taurine, the simplest β-aminosulfonic acid, is a class of organic molecules with important biological functions (Liebowitz, S.M.; Lombardini, J.B.; Salva, P.S.Biochem.Pharmac.1988, 37, 1303), and also a class of important Nutrients, widely used as food additives, etc. Taurine is also one of the essential amino acids for the human body. It can be used to prevent and treat colds, fever, neuralgia, tonsil inflammation, rheumatoid arthritis, cholecystitis, congestive heart failure, high blood pressure, drug poisoning, re...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C303/16C07C309/15
Inventor 许家喜胡立博杜大明
Owner PEKING UNIV
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