Method for preparing substituted homotaurine from alpha, beta-unsaturated amide

A high taurine, unsaturated technology, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc., can solve the problems of raw material limitation, troublesome desalination and purification process, etc., and achieve the effect of simple operation

Active Publication Date: 2012-09-12
BEIJING UNIV OF CHEM TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] These existing methods can be used to synthesize homotaurine or substituted homotaurine, but often due to the limitation of raw materials, only certain structural types of substituted homotaurine can be synthesized, or troublesome desalination and purification processes are required

Method used

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  • Method for preparing substituted homotaurine from alpha, beta-unsaturated amide
  • Method for preparing substituted homotaurine from alpha, beta-unsaturated amide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0045] 1-Amino-3-butanesulfonic acid 4a preparation of

[0046] In a 50 mL three-necked flask, 0.851 g (10 mmol) of 2-butenamide was added to 15 mL CH 2 Cl 2 , followed by dropwise addition of 5 drops of anhydrous triethylamine. Heated to reflux under nitrogen protection, added dropwise 0.952 g (12.5 mmol) of thioacetic acid, and refluxed for 20 h. Cool to room temperature, remove the solvent and then separate by silica gel column chromatography [petroleum ether (PE): ethyl acetate (EA) = 1:2, v / v] to obtain 1.251 g of intermediate 3-acetylthiobutyramide, yield 77.6% .

[0047] In a 100 mL single-necked bottle, 1.520 g (40 mmol) LiAlH 4 Add to 30 mL of anhydrous THF. Then 5 mL THF solution containing 0.645 g (4 mmol) 3-acetylthiobutyramide was added dropwise, heated to reflux for 18 h, and quenched with water in an ice-water bath after returning to room temperature, then added 10 mL of water and stirred for 12 h. Filtration, filtrate with CH 2 Cl 2 Three extracti...

Embodiment 2

[0049] 2-Methyl-3-aminopropanesulfonic acid 4b preparation of

[0050] According to the method described in Example 1, 2-methacrylamide was used instead of 2-butenamide as a raw material to obtain a colorless crystal intermediate of 2-methyl-3-acetylthiopropionamide with a yield of 95%. Melting point 84-86 o C; Colorless crystals of 2-methyl-3-aminopropanesulfonic acid were obtained after reduction and oxidation, yield 70%, melting point 234-238 o c. Literature melting point: 260-265 o c. 1 H NMR (400 MHz, D 2 O) δ: 3.15 (dd, J = 6.0, 13.2 Hz, 1H in SCH 2 ), 2.93 (dd, J = 6.8, 14.4 Hz, 1H in NCH 2 ), 2.90 (dd, J = 6.8, 13.2 Hz, 1H in SCH 2 ), 2.87 (dd, J= 6.0, 14.4 Hz, 1H in NCH 2 ), 2.32 (ttq, J = 6.8, 6.0,6.8 Hz, 1H, CH), 1.10 (d, J = 6.8 Hz, 3H, CH 3 ); 13 C NMR (100 MHz, D 2 O) δ: 54.7, 44.2, 28.7, 17.0; IR n (cm -1 ): 3451 (br, s, NH, OH), 1280 (SO), 1176 (SO).

Embodiment 3

[0052] 2-Methyl-1-amino-3-butanesulfonic acid 4c preparation of

[0053] According to the method described in Example 1, with 2-methyl-2-butenamide instead of 2-butenamide as raw material, 2-methyl-3-acetylthiobutyramide was obtained with a yield of 75%. Crystal intermediate, melting point 136-138 o C; After reduction and oxidation, oily 2-methyl-1-amino-3-butanesulfonic acid was obtained in 40% yield. 1 H NMR (400 MHz, D 2 O) δ: 3.27 (dd, J = 5.6, 13.2 Hz, 1H in NCH 2 ), 2.96 (dq, J = 2.8, 7.2 Hz, 1H, SCH), 2.82 (dd, J = 8.4, 13.2 Hz, 1H in NCH 2 ), 2.42 (dddq, J = 2.8, 5.6, 8.4, 7.2 Hz, 1H, CH), 1.21 (d, J = 7.2 Hz, 3H, CH 3 ), 1.05 (d, J = 7.2 Hz, 3H, CH 3 ); 13 C NMR (100 MHz, D 2 O) δ: 58.5, 41.2, 32.3, 15.4, 9.8; IR n (cm -1 ): 2976 (br, s, NH, OH), 1205 (SO), 1030 (SO). HRMS (ESI, m / z ) calcd. for C 5 h 13 NO 3 S [M+H] + m / z : 168.0689; found: 168.0682.

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Abstract

The invention provides a method for preparing substituted homotaurine from an alpha, beta-unsaturated amide. The method is characterized in that thioacetic acid and the alpha, beta-unsaturated amide undergo an addition reaction to produce corresponding 3-acetylthioacetamide and through reduction and oxidation, the substituted homotaurine is obtained. The method adopts simple and easily available raw materials, is convenient for operation, avoids a complicated desalting purification process, and is especially suitable for large-scale industrial production. The homotaurine can be used as a nutriment, a drug, an enzyme inhibitor, an antiseptic, a surfactant, a plant-growth regulator and a raw material of sulfonopeptides.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of substituted homotaurine. Background technique [0002] Homotaurine, or 3-aminopropanesulfonic acid, is an aminoalkylsulfonic acid isolated from Centipede lingulae, which is structurally similar to the neurotransmitter γ-aminobutyric acid, and it has been found to have Anticonvulsant efficacy of gamma-aminobutyric acid (Fariello, R. G.; Golden, G. T.; Pisa, M. Neurology 1982, 32 , 241). Hypertaurine can also prevent and treat sclerosis of the conjunctival sheath, prevent hair loss, treat alcohol dependence, inhibit the oxidation of catecholamines in the body, protect DNA from oxidative damage, improve memory, strengthen the heart, and lower blood pressure (Mayer, J. ; Cook, A.M. J. Bacteriol . 2009, 191 , 6052; Rouhani, S.; Dallava Santucci, J.; Bajenaru, O.; Emmanouilidis, E.; Tran, G.; Pharmacol., Biochem. Behav . 1998, 59 ,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14C07C309/24C07C303/16
Inventor 许家喜奈有峰
Owner BEIJING UNIV OF CHEM TECH
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