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

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: 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 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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  • A method for preparing substituted homotaurine from α, β-unsaturated amides

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0041] Preparation of 1-Amino-3-酸 Sulfate 4A

[0042] In the 50 ml three-port bottle, add 2-clutlamide 0.851 g (10 mmol) to 15 ml CH 2 CL 2 In the middle, dripped 5 drops of water -free triama.Heated under the protection of nitrogen to return, adding 0.952 g (12.5 mmol) with sulfur sulfur and 20 h.Cool to room temperature, separate the silicone column chromatography after removing the solvent [Petroleum ether (PE): ethyl acetate (EA) = 1: 2, V / V] to get the intermediate 3-acetyl-base butadamide 1.251 g, 77.6% of the income rate of 77.6%Essence

[0043] Among the 100 mL single -mouth bottle, 1.520 g (40 mmol) lialh under the ice water bath 4 Add to 30 ml of waterless THF.Subsequently, a 5 ml THF solution containing 0.645 g (4 mmol) 3-acetyl-sulfonicide, heating and returning 18 h, quenched with water under the ice water bath after recovery room temperature, and added 10 mL water to stir for 12 h.Filter, CH with the filter fluid 2 CL 2 Extract three times (10 ml ′ 3) to get yellow o...

Embodiment 2

[0045] Preparation of 2-methyl-3-amino propylsulfonate 4B

[0046] According to the method described in the Example 1, 2-methyl acrylamide instead of 2-butanlamide as the raw material, and the 95%yield obtained 2-methyl-3-acetyl sulfurine-free crystal intermediate.Following point 84-86 o C; after restore and oxidation, get colorless crystal 2-methyl-3-amino propyl, 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, D, J = 6.8 Hz, 3H, CH 3 ); 13 C nmr (100 mHz, D2 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

[0048] Preparation of 2-methyl-1-amino-3-丁 sulfate 4C

[0049] According to the method described in the Example 1, 2-methyl-2-butanlamide is used instead of 2-butanlamide as the raw material.Crystal intermediate, melting point 136-138 o C; after restore and oxidation, obtain an oily 2-methyl-1-amino-3-bute sulfonic acid, with an yield of 40%. 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 is an organic synthetic technology field, which involves the preparation method of replacing high taurine. Background technique [0002] High taurine, that is, 3-aminoopate, is a kind of amino alkyl sulfonic acid separated from tongue-shaped coriander algae.γ-aminobutyric acid anti-ricoring effect (Fariello, R. G.; G. T.; PISA, M. Neurnogy 1982, 32 , 241).High taurine can also prevent and treat the hardening of conjunctival sheaths, prevent hair loss, treat alcohol dependence, inhibit the oxidation of catecholamine in the body, protect DNA from oxidation damage, improve memory, strong heart, lower blood pressure, etc. (Mayer, J. J.; COOK, A. M. J. Bacteriol . 2009, 191 , 6052; Rouhani, S.; Dallava Santucci, J.; Bajenaru, O.; Emmanouilidis, E.; TRAN, G.; Manicom, R.; Dinh-xuan, a. t.; Per. Pharmacol., Biochem. Behav . 1998, 59 , 955; biasetti, m.; Dawson, r. jr. Amino Acids. 2002, 22 , 351; MESSINA, S. A.; DAWSON, R. Jr. Adv. Exp. Med. Biol. 20...

Claims

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Application Information

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