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A method for preparing 1-substituted homotaurine from α, β-unsaturated nitrile

A high taurine, unsaturated technology, applied in sulfonic acid preparation, 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: 2015-10-14
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 its derivatives, 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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  • A method for preparing 1-substituted homotaurine from α, β-unsaturated nitrile
  • A method for preparing 1-substituted homotaurine from α, β-unsaturated nitrile

Examples

Experimental program
Comparison scheme
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Embodiment 1

[0038] 1-Amino-3-butanesulfonic acid 4a preparation of

[0039] Dissolve 5 mmol of α,β-unsaturated nitrile in 20 mL of toluene, add catalytic amount of base Bu 3 N, nitrogen protection, control the temperature at 75-85 o Between C, 456 mg (6 mmol) of thioacetic acid was added dropwise, and reacted at this temperature for 6 h. Reaction finishes and removes solvent, separates by silica gel column chromatography (petroleum ether: ethyl acetate=8:1 is eluent), product R f Between 0.55-0.65, the brownish-red oily addition product cyanothiol acetate shown in formula 2 was obtained, with a yield of 46%.

[0040] 8 mmol LiAlH 4 Dissolve in 20 mL of anhydrous ether, and slowly add 10 mL of 0.1 mol / L ether solution of cyanothiol acetate dropwise under ice-water bath. After the dropwise addition, stirring was continued for 2 h in an ice-water bath. After the reaction is complete, add water to quench, filter out insoluble impurities, and use CH 2 Cl 2 Extract with ethyl acetate, c...

Embodiment 2

[0042] 1-Phenyl-3-propanesulfonic acid 4b preparation of

[0043] According to the method described in Example 1, using cinnamonitrile as a raw material, a light yellow crystal addition product was obtained with a yield of 42%, m.p.76-77 o C; After reduction and oxidation, a colorless solid product was obtained with a yield of 64%. m.p. 313-314 o C; 1 H NMR (400 MHz, D 2 O) δ : 7.34 (s, 5H, ArH), 4.03 (dd, J = 4.8, 10.8 Hz, 1H, CHSO 3 ); 2.93 (ddd, J = 4.8, 10.8, 10.8 Hz, 1H in CH 2 N); 2.76 (ddd, J = 4.8, 10.8, 10.8 Hz, 1H in CH 2 N); 2.50 (dddd, J = 4.8, 4.8, 10.8, 10.8 Hz, 1H in CH 2 ); 2.35 (dddd, J = 4.8, 10.8, 10.8, 10.8 Hz, 1H in CH 2 ). 13 C NMR (100 MHz, D 2 O / HCO 2 h) δ :28.3, 37.5, 63.4, 128.7, 128.9, 129.1, 134.4. IR ( ν , cm -1 ): 3406.8 (br, s, OH, NH), 1238.1 (S=O), 1177.0 (S=O). HRMS (ESI) Calcd. for C 9 h 14 NO 3 S [M+H] + m / z : 216.0694; Found 216.0691.

Embodiment 3

[0045] 1-p-methylphenyl-3-propanesulfonic acid 4c preparation of

[0046] According to the method described in Example 1, using p-methylcinnamonitrile as a raw material, a light yellow crystal addition product was obtained with a yield of 31%, m.p.68-69 o C; After reduction and oxidation, a colorless solid product was obtained with a yield of 82.3%; m.p. 350-352 o C; 1 H NMR (400 MHz, D 2 O) δ : 2.16 (s, 3H, CH 3 ), 2.25 (dddd, J = 5.2, 10.4, 10.4, 13.6 Hz, 1H in CH 2 ), 2.41 (dddd, J = 4.8, 6.0, 10.4, 13.6 Hz, 1H in CH 2 ), 2.66 (ddd, J = 5.2, 10.4, 12.4 Hz, 1H in CH 2 N), 2.84 (ddd, J = 6.0, 10.4, 12.4 Hz, 1H in CH 2 N), 3.91 (dd, J = 4.8, 10.4 Hz, 1H, CHSO 3 ), 7.09-7.17 (m, 4H, ArH). 13 C NMR (D 2 O / HCO 2 h) δ: 14.8, 22.9, 32.1, 57.6, 123.6, 124.0, 125.9, 133.5. IR ( ν , cm -1 ): 3423.1 (br, s, OH, NH), 1208.2 (S=O), 1169.9 (S=O). HRMS (ESI) Calcd. for C 10 h 15 NNaO 3 S [M+Na] + m / z : 252.0670; Found 252.0678.

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Abstract

The invention provides a method for preparing 1-substituted tramiprosate from alpha, beta-unsaturated nitrile. The method comprises the following steps of: performing addition on alpha, beta-unsaturated nitrile through thioacetic acid to obtain corresponding cyano mercaptan acetate; and performing reduction and oxidation to obtain 1-substituted tramiprosate. The preparation method has the advantages of simple and readily available raw materials, convenience in operation, no need of complex desalting purification process and particular suitability for large-scale industrial production. The obtained compound can be used as a nutrient substance, a medicament, an enzyme inhibitor, an antibacterial agent, a surfactant, a plant growth regulator, a raw material for preparing sulphonyl peptide and the like.

Description

technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a preparation method of 1-substituted homotaurine. Background technique [0002] Homotaurine, or 3-aminopropanesulfonic acid, is an aminoalkylsulfonic acid that is structurally similar to the neurotransmitter gamma-aminobutyric acid, which has been found to have the anticonvulsant properties 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 , 955; Biasetti, M.; Daws...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C309/14C07C303/02
Inventor 许家喜马云海
Owner BEIJING UNIV OF CHEM TECH