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Tartaric acid ester compound as well as preparation method and applications thereof
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A compound and catalyst technology, applied in the application of tartrate thioester compounds in titanium-catalyzed sulfide oxidation reaction, the field of tartrate thioester compounds and their preparation, can solve problems such as adverse effects of the main reaction
Active Publication Date: 2019-03-15
JIANGSU AOSAIKANG PHARMA CO LTD
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[0006] In the prior art, there is no research and report about using sulfur-containing compounds as ligands for asymmetric oxidation of thioethers, because based on the common knowledge in this field, the asymmetric oxidation reaction of thioether substrates is sensitive to temperature, moisture, alkali and Catalysts and other conditions are very sensitive, and sulfur-containing organic compounds such as thioethers and thioesters are easily oxidized substances (tetrahedron Letters, Vol 33, No.4, pp 469-470, 1992; Polyhedron 53 (2013), 172 -178), when used as a ligand for an asymmetric oxidation reaction, it is easily oxidized and has an adverse effect on the main reaction. Therefore, it is generally believed that sulfur-containing compounds are not suitable as a ligand for asymmetric oxidation reactions Related research
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Embodiment 1-4
[0072] Examples 1-4 Ligand compounds were synthesized according to Scheme 1.
[0073]
Embodiment 1
[0074] Synthetic (R is ethyl) of embodiment 1 ligand compound Ia
[0075] Into a 100ml flask, compound II (4.4g, 20mmol), 50ml of methanol (dried), and lithiumhydroxide monohydrate (2.0g, 48mmol) were successively added, and stirred at room temperature for 24h. After concentration, the product was pumped dry at 50°C to obtain compound III as a white solid.
[0076] Add compound III (4.0g, 20mmol), 40ml tetrahydrofuran (dry), crown ether (18-crown-6, 20mg) to a 100ml flask in turn, and add trimethylchlorosilane (7.6ml, 60mmol) dropwise at room temperature. Continue to stir at room temperature for 3 h, concentrate and drain to obtain oily compound IV.
[0077] Add 40ml of dry tetrahydrofuran and DMF (2 drops) to the obtained compound IV, add oxalyl chloride (5.1ml, 60mmol) dropwise at room temperature, continue stirring at room temperature for 1h, concentrate and drain to obtain compound V, add 20ml of dry tetrahydrofuran for later use.
[0081] Synthetic (R is benzyl) of embodiment 2 ligand compound 1b
[0082] The synthesis of ligand Ib is referred to Example 1, the difference is that benzylthiol replaces ethanethiol. Compound Ib was obtained as a white solid. The overall yield is 27%.
[0083] 1 H NMR (400MHz, CDCl 3 )δ7.34–7.24(m,10H),4.68(d,J=8Hz,2H),4.19(d,J=12Hz,2H),4.16(d,J=8Hz,2H),3.38(brs,1H ),3.36(brs,1H).
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Abstract
The invention discloses a compound shown in formula (I), wherein R1 and R2 are independently selected from optionally substituted C1-6 alkyl, optionally substituted C3-8 cycloalkyl, optionally substituted C6-14 aryl and optionally substituted -(CH2)m-C3-8 cycloalkyl or -(CH2)n Ar; and Ar denotes the optionally substituted C6-14 aryl. The compound can be used for preparing prazole drugs during thetitanium-catalyzed asymmetric oxidation of pyrazole sulfides. (img file='DDA0001401304200000011.TIF' wi='669' he='551' / ).
Description
technical field [0001] The invention belongs to the technical field of organic synthesis, and in particular relates to a tartratethioester compound and a preparation method thereof, and the application of the tartratethioester compound in titanium-catalyzed sulfide oxidation reaction. Background technique [0002] The asymmetric oxidation of thioethers is a key step in the synthesis of many chiral sulfoxide drugs (such as proton pump inhibitors S-omeprazole, R-rabeprazole, etc.), and has been very active in the past three decades Research areas. Most asymmetric thioether oxidations are metal catalyzed, the most common being titaniummetal, although there are also many metal-free catalyzed oxidations and biological oxidations. [0003] The main titanium-catalyzed sulfide asymmetric oxidation methods in the prior art include: [0004] In 1984, the Kagan group improved the Sharpless oxidation system and found an efficient asymmetric oxidation system for common thioethers (J...
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