Method for preparing ergocalciferol double-projection product

A vitamin and double-protection technology, which is applied in the field of preparation of vitamin D2 double-protection products, can solve the problems of difficult processing, cumbersome post-processing, and unfavorable industrialization, and achieve the effect of reducing solvent costs and energy consumption

Inactive Publication Date: 2013-07-10
WUHAN QR PHARMA CO LTD +1
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  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

The shortcoming of this method is that post-treatment is more complicated, and the reagent dimethylformamide is difficult to handle compared with dichloromethane, and column chromatography is also used, which is not conducive to industrialization

Method used

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  • Method for preparing ergocalciferol double-projection product

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Dissolve vitamin D2 12.5g (31.6mmol) in 100ml of dichloromethane, add it to a sufficient amount of liquid sulfur dioxide, protect it with argon, keep the temperature at -25°C for 1.5h, then put it at room temperature for 0.5h, heat React at 30°C for 0.5h; directly add 5.0g (33.2mmol) of tert-butyldimethylsilyl chloride (TBDMSC1) and 3.2g (47.4mmol) of imidazole, stir for 2h, post-process, evaporate to dryness to obtain a light yellow solid, Adding n-hexane for multiple recrystallizations gave 17.5 g of vitamin D2 double-protected product (compound 1), with a yield of 96.5% (yield calculated as vitamin D2).

Embodiment 2

[0029] Dissolve vitamin D2 12.5g (31.6mmol) in 100ml of dichloromethane, add it to a sufficient amount of liquid sulfur dioxide, protect it with argon, keep the temperature at -10°C for 2.0h, then put it at room temperature for 1.0h, heat React at 40°C for 0.75h; directly add 5.2g (34.8mmol) of tert-butyldimethylsilyl chloride (TBDMSC1) and 4.7g (69.5mmol) of imidazole, stir for 2h, post-process, evaporate to dryness to obtain a light yellow solid, Adding n-heptane for multiple recrystallizations gave 17.5 g of vitamin D2 double-protected product (compound 1), with a yield of 97.8% (yield calculated as vitamin D2).

Embodiment 3

[0031] Dissolve 25g (63.1mmol) of vitamin D2 in 200ml of dichloromethane, add it to a sufficient amount of liquid sulfur dioxide, protect it with argon, keep the temperature at -10°C for 2.0h, then put it at room temperature for 1.0h, and heat to React at 40°C for 1.0h; directly add 10.4g (69.6mmol) of tert-butyldimethylsilyl chloride (TBDMSC1) and 9.4g (139.0mmol) of imidazole, stir for 2.0h, post-process, evaporate to dryness to obtain a light yellow solid, Adding n-heptane: n-hexane = 20:1 for multiple recrystallizations gave 17.5 g of vitamin D2 double-protected product (compound 1), with a yield of 98.1% (yield calculated as vitamin D2).

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Abstract

The invention discloses an improved method for preparing an ergocalciferol double-projection product, which is characterized by comprising the following steps: a) adding ergocalciferol in liquid sulfur dioxide, and respectively reacting at minus 25-minus 10 DEG C, at room temperature and at 30-40 DEG C; b) directly adding tert-Butyldimethylsilyl chloride and imidazole to react; and c) adding alkane solvent, and recrystallizing to obtain a target product. The invention adopts a one-pot method to merge at two-step reaction into one-step reaction, thus lowering the solvent cost and reducing other energy consumption at the same time; and a recrystallization method instead of column chromatograph is adopted to obtain the target product so as to enable the method to be applicable to industrialized production in technology.

Description

technical field [0001] The present invention relates to the production of vitamin D2 double protection product (9.10-ring-opened cholesteryl-5,7(E)10,19,22(E)-tetraene-3S-tert-butyldimethylsilyl ether sulfur dioxide adduct) Preparation. Background technique [0002] Vitamin D in the classical sense refers to some sterol substances for the treatment and prevention of rickets, including vitamin D2 and calciferol, vitamin D3 and vitamin D1 (or vitamin D4). Vitamin D2 and vitamin D3 have an important impact on calcium and phosphorus metabolism and bone growth in children. They can promote calcium and phosphorus absorption in the intestine and normal bone calcification. They are the main drugs for the treatment of rickets, rickets and hypothyroidism clinically. [0003] Although vitamin D2 and vitamin D3 have the same effect, they have different activity strengths. In comparison, the strength of vitamin D3 is greater than that of vitamin D2, and some active metabolites of vitami...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07F7/18
Inventor 路生辉单晓燕时惠麟陈旭东王朝东刘勇
Owner WUHAN QR PHARMA CO LTD
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