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A technology of derivatives and vitamins, applied in the field of preparation of vitamin D2 derivatives, can solve the problems of reducing the yield of calcipotriol and having no utilization value, and achieves the effects of low cost of raw materials, improved utilization, and reduced pollution
Inactive Publication Date: 2010-10-27
ZHEJIANG JINGXIN PHARMA
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[0005] The reduction process of the above-mentioned method mainly obtains the undesired C-24 hydroxyl epimer alcohol (compound III, usually containing about 60%), which greatly reduces the yield of calcipotriol (compound II), and C-24 Hydroxy epimer alcohol (compound III) is a waste intermediate and currently has no utilization value
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Embodiment 1
[0021] Add 5.0 g (0.0078 mol) of compound (III) and 100 ml of toluene, stir to dissolve, add 4.4 g (0.0117 mol) of PDC, heat to reflux at 110 ° C, keep warm for 6 h, TLC test confirms that the reaction is complete, and the developer is petroleum ether: Ethyl acetate = 9:1, cool down to room temperature to stop the reaction, add an appropriate amount of column chromatography silica gel to the floxacin funnel, filter the reaction solution, evaporate to dryness to obtain an oil, and separate by column chromatography to obtain 4.3 g of compound (I), with a yield of 86.3 %.
Embodiment 2
[0023] Put in 5.0g (0.0078mol) of compound (III) and 100ml of N,N'-dimethylformamide, stir to dissolve, add 4.4g (0.0117mol) of PDC, heat to reflux at 120°C, keep the reaction for 4h, and cool down to room temperature Stop the reaction, add an appropriate amount of silica gel for column chromatography into the floxacin funnel, filter the reaction solution, and evaporate to dryness to obtain an oily substance, which is separated by column chromatography to obtain 4.1 g of compound (I), with a yield of 82.3%.
Embodiment 3
[0025] Put in 5.0g (0.0078mol) of compound (III) and 100ml of chloroform, stir to dissolve, add 20g of manganese dioxide, heat to 70°C for reflux reaction for 24h, cool down to stop the reaction, add an appropriate amount of column chromatography silica gel to the Shaxing funnel, and the reaction solution After filtering and evaporating to dryness to obtain an oil, 4.0 g of compound (I) was obtained by column chromatography with a yield of 80.3%.
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Abstract
The invention discloses a method for preparing a vitamin D2 derivative. In the conventional method for preparing Calcipotriol, C-24 hydroxy epimeric alcohol (a compound III) is mainly obtained, the yield of the Calcipotriol is greatly reduced, and the C-24 hydroxy epimeric alcohol is a waste intermediate and does not have any utilization value so far. In the method of the invention, the waste intermediate compound III generated in the conventional process of preparing the Calcipotriol is taken as a starting material, and the method comprises the following steps of: in an organic solvent and in the presence of an oxidizer capable of oxidizing hydroxyl into carbonyl, performing heat preservation reaction at the temperature of between 20 and 120 DEG C, after complete reaction, cooling to room temperature, and treating to obtain a compound I; and performing reduction reaction on the compound I to obtain a compound II, namely the Calcipotriol. In the method, the waste intermediate compound III is recycled, the cost of raw materials is low, the utilization rate of the materials is improved, and the pollution is reduced; and by combining the conventional preparation process, the method can obviously improve the yield of the Calcipotriol in the conventional preparation process.
Description
technical field [0001] The invention relates to the field of medicinal chemistry, in particular to a preparation method of vitamin D2 derivatives. Background technique [0002] Calcipotriol (catclpotr[o1) is an analog of vitamin D3 active metabolite calcitriol (calcitr[o1), whose synthesis was first reported by Ca[verley (1988), developed and produced by Leo Denmark in 1991 Available in the UK, Denmark and Ireland in March. Calcipotriol synonym calcipotriene, Mc903.dovonex, da Evonex, chemical name (1α, 3β, 5z, 7e, 22e, 24s)-24-cyclopropyl-9,10-blocked cholesterol-5,7, 10(19), 22-tetraene-1, 3, 24-triol, vitamin D3 is continuously hydroxylated in the liver and kidney to become an important active metabolite 1,25(OH)2-D, calciferol alcohol. Studies have shown that in addition to having a strong effect on calcium absorption, calcitriol can also regulate the proliferation and differentiation of certain cells, including epidermal keratinocytes. As a new anti-psoriasis drug, ...
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