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Method for preparing substituted taurine

A technology of taurine and sulfuric acid, applied in the preparation of organic compounds, chemical instruments and methods, organic chemistry, etc., can solve problems such as lack of further development and application, unfavorable substitution reactions, and lack of raw materials

Inactive Publication Date: 2010-10-27
PEKING UNIV
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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 effectively synthesize substituted taurine, there are often many steps or the raw materials used are not commercially available, so you need to prepare them yourself
And the ethanolamine that people such as Rumpf establishes is prepared into vitriol, then replaces with sodium sulfite or sodium bisulfite etc. to prepare the method for taurine (Rumpf, P.Bull.Soc.Chim.Fr., 1965,945-6; Senoo, A.; Enomoto, T.; Nagata, T.Jpn. Kokai Tokkyo Koho JP 93-323741; Xu Guoxian, Wang Zaixin, Ye Feng, Chinese Invention Patent Publication, CN1385420A; CN 1626511A) is simple and effective, but has not been further developed and applied all the time. It is only used for the synthesis of taurine itself, but not applied to the preparation of other substituted taurines
It is speculated that the reason may be that technical prejudice makes people think that the sulfuric acid monoesters of amino alcohols other than aminoethanol are not conducive to the occurrence of substitution reactions due to steric hindrance or solubility.

Method used

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  • Method for preparing substituted taurine
  • Method for preparing substituted taurine
  • Method for preparing substituted taurine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0055] Preparation of (S)-2-amino-3-phenylpropylsulfonic acid (1a)

[0056] (1) Esterification:

[0057]A mixture of ice-cold 4g concentrated sulfuric acid and 4mL water was added under cooling in an ice-water bath into a 50mL round-bottomed flask containing 6.05g (40mmol) (S)-2-amino-3-phenyl-1-propanol and 4mL water, Heating to 120-130°C with stirring, and distilling off the water under reduced pressure to obtain a colorless or slightly yellow solid or oily aminoalcohol sulfuric acid monoester. Colorless crystals can be obtained after recrystallization from ethanol, but purification is generally not required.

[0058] (2) replace:

[0059] Dissolve the sulfuric acid monoester obtained above in 80 mL of water, add 7.56-10.08 g (60-80 mmol) of sodium sulfite, and stir and react at 0-100° C. for 12-72 hours. The solvent was distilled off, and the residue was recrystallized from methanol or a mixture of methanol and ether to obtain a colorless crystalline product, substituted...

Embodiment 2

[0061] Preparation of (S)-2-amino-2-phenylethylsulfonic acid (1b)

[0062] According to the method described in Example 1, (S)-2-amino-2-phenylethylsulfonic acid was obtained from (S)-2-amino-2-phenylethanol as a colorless crystal with a melting point of 332°C , The two-step total yield is 30-69%. [α] D 20 = -1.3 (c 1.00, HCO 2 H). 13 CNMR (50MHz, HCO 2 H)δ: 57.6, 62.7, 127.4, 129.4, 129.9, 132.8.

Embodiment 3

[0064] Preparation of (S)-3-methyl-2-amino-butylsulfonic acid (1c)

[0065] According to the method described in Example 1, (S)-3-methyl-2-aminobutanol was used as raw material to obtain (S)-3-methyl-2-amino-butylsulfonic acid, colorless crystals, melting point 325~326℃, two-step total yield 70%.[α] D 20 =+29.7(c1.01, HCO 2 H). 13 CNMR (75.5 MHz, HCO 2 H)δ: 16.2, 17.1, 30.3, 49.3, 54.6.

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Abstract

The present invention provides one substituted taurine preparing process, in which substituted taurine is prepared with o-amino alcohol as material and through esterification with sulfuric acid and substitution with sulfite or bisulfite. The process has facile material and simple operation, and is suitable for industrial production of substituted taurine, including optically active substituted taurine. The produced substituted taurine may be applied as nutritive matter, medicine, enzyme inhibitor, antiseptic, surfactant, plant growth regulator, etc.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of substituted taurine. Background technique [0002] Sulfamic acid is a class of naturally occurring sulfur-containing amino acids (Timothy, C.; Birdsall, N.D.Alt.Med.Rev.1998, 3, 128), and also an important analogue of a class of natural amino acids with a tetrahedral structure (Xu Jiaxi , Organic Chemistry, 2003, 23, 1). The simplest β-aminosulfonic acid is taurine, 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 also an important nutrient substance, widely used as a food additive. It can also be used to prevent and treat colds, fever, neuralgia, tonsil inflammation, rheumatoid arthritis, cholecystitis, congestive heart failure, high blood pressure, drug p...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/19C07C303/14C07C309/24
Inventor 许家喜张威王博远陈宁杜大明
Owner PEKING UNIV