Derivative of substitutional taurine and preparation method

A taurine derivative, selected technology, applied to the preparation of sulfonic acid, preparation of organic compounds, chemical instruments and methods, etc., to achieve the effect of easy preparation and easy access to raw materials

Inactive Publication Date: 2005-11-16
PEKING UNIV
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

There is no general preparation method for 1-substituted taurine, and only 2-aminosulfinyl chloride (Moree, W.J.; van der Marel, G.A.; Liskamp , R.M.J.J.Org.Chem.1995, 60, 5157; Lowik, D.W.P.M.; Liskamp, ​​R.M.J.Eur.J.Org.Chem.2000, 1219)

Method used

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  • Derivative of substitutional taurine and preparation method
  • Derivative of substitutional taurine and preparation method
  • Derivative of substitutional taurine and preparation method

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0057] Preparation of 1-N, N-diethylamino-3-phenoxypropane-2-sulfonic acid (1a)

[0058] (1) ring vulcanization:

[0059] Add 5.0g (33mmol) of 2-phenoxymethyloxirane, 34g (175mmol) of potassium thiocyanate-silica gel mixture and 100mL toluene into a 250mL three-necked flask, stir, and maintain a reflux state. TLC monitoring (petroleum ether-ethyl acetate 3:1, v / v, silica gel plate, ethylene oxide R f =0.50, sulfide R f =0.67), after 5h, the raw material point disappeared, and the reaction was stopped. The solid was filtered off with a quartz sand funnel, and the solvent was spun off at 60° C. to obtain 5.3 g of 2-phenoxymethylthioethane as a light yellow liquid, with a yield of 96 %. The yield without the catalyzed potassium thiocyanide-silica gel mixture was 86%.

[0060] (2) Amine ring opening:

[0061] Add a solution of diethylamine (6.57g, 90mmol) in 100mL of benzene-ethanol (the general ratio is 1:9 to 9:1) into a 250mL round bottom flask, and control the temperature...

Embodiment 2

[0065] Preparation of 1-N, N-dibenzylamino-3-phenoxypropane-2-sulfonic acid (1b)

[0066] According to the method described in Example 1, dibenzylamine was used to open the ring to obtain 1-N, N-dibenzylamino-3-phenoxy-2-propanethiol, a colorless liquid, and the yield was 75%. 1 H NMR (200MHz, CDCl 3 )δ7.45-6.80 (m, 15H, ArH), 4.08 (dd, J=5.2, 9.5Hz, 1H in OCH 2 ), 3.91 (dd, J=6.2, 9.5Hz, 1H in OCH 2 ), 3.62(s, 4H, 2NCH 2 ), 3.45 (dddd, J=5.2, 6.2, 7.2, 7.6Hz, 1H, SCH), 2.86 (ddd, J=7.6, 13.2Hz, 1H in NCH 2 ), 2.60 (dd, J=7.2, 13.2Hz, 1H in NCH 2 ), 1.59 (s, br, 1H, SH). 13 C NMR (50MHz, CDCl 3 )δ158.5, 138.9, 129.5, 129.1, 128.3, 127.2, 121.0, 114.6, 70.8, 58.8, 57.6, 37.9.

[0067] Starting from 1-N,N-dibenzylamino-3-phenoxy-2-propanethiol, the oxidation method described in Example 1 was used to prepare 1-N,N-dibenzylamino-3-phenoxy propane-2-sulfonic acid. Colorless crystals, mp 199-201°C, yield 81%. 1 H NMR (200MHz, CDCl 3 )δ10.34 (s, br, 1H, SO 3 H), 7.62-6.71...

Embodiment 3

[0069] (S)-1-N, Preparation of N-dibenzylamino-3-phenoxypropane-2-sulfonic acid (1c)

[0070] According to the method described in Example 2, (S)-2-phenoxymethyl oxirane is used as raw material to obtain (R)-2-phenoxymethyl sulfide, and dibenzylamine ring-opening obtains ( S)-1-N, N-dibenzylamino-3-phenoxy-2-propanethiol, colorless liquid, yield 78%.[α] 20 D =+4.2(c 1.10, CHCl 3 ). 1 H NMR (200MHz, CDCl 3 )δ7.38-6.78 (m, 15H, ArH), 4.07 (dd, J=4.8, 9.2Hz, 1H in OCH 2 ), 3.91 (dd, J=3.2, 9.2Hz, 1H in OCH 2 ), 3.61 (s, 4H, 2NCH 2 ), 3.41 (dddd, J=3.2, 4.8, 7.2, 7.6Hz, 1H, SCH), 2.85 (dd, J=7.6, 13.0Hz, 1H in NCH 2 ), 2.59 (dd, J=7.2, 13.0Hz, 1H in NCH 2 ), 2.02(s, br, 1H, SH). 13 C NMR (50MHz, CDCl 3 )δ158.5, 138.9, 129.4, 129.0, 128.3, 127.2, 121.0, 114.6, 70.7, 58.8, 57.6, 37.9.

[0071] According to the method described in Example 1, (S)-1-N, N-dibenzylamino-3-phenoxy-2-propanethiol was oxidized to obtain (S)-1-N, N-dibenzyl Amino-3-phenoxypropane-2-sulfonic acid....

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Abstract

A substituted taurine derivative used as nutrient, medicine, enzyme depressant, antibacterial agent, surfactant, etc is prepared from substituted epoxy ethane through cyclosulfurizing, opening, ring, oxidizing and hydrogenolyzing.

Description

Technical field: [0001] The invention belongs to the technical field of organic compounds and organic synthesis, and specifically relates to a new class of substituted taurine derivatives and a preparation method thereof. Background technique: [0002] Sulfamic acid, as an important analogue of a class of natural amino acids with a tetrahedral structure, has attracted much attention in recent years (Xu Jiaxi, Organic Chemistry, 2003, 23, 1). β-Sulfamic acid can be regarded as a substituted taurine, and it is also an important raw material and monomer for the synthesis of sulfonyl peptides. Taurine is a class of molecules with important biological functions (Liebowitz, S.M.; Lombardini, J.B.; Salva, P.S. Biochem. Pharmac. 1988, 37, 1303), is also a class of important nutrients, widely used as food additives and so on. Research on the biological function of sulfamic acid has found that some sulfamic acid has anticancer and antiviral activity (Neelakantan, L.; Hartung, W.H.J.O...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C309/14
Inventor 许家喜黄家兴杜大明
Owner PEKING UNIV
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