Method for synthesizing 5-trifluoro methyl-2'-desugarized uridine

A technology of deoxyuridine and trifluoromethyl, applied in sugar derivatives, organic chemistry, etc., can solve the problems of easy pollution of the environment, and achieve the effect of simple operation, easy availability of synthetic raw materials, and high purity

Inactive Publication Date: 2007-08-29
FUBANG BIO PHARMA HANGZHOU
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

5-trifluoromethyl-2', 3'-dideoxyuridine was developed by Bayer, and in Chinese patent application 92102448.7, a synthetic 5-trifluoromethyl-2', 3'-dideoxyuridine was disclosed The method of glucoside, it is starting raw material with ethyl trifluoropropionate, needs to use tin tetrachloride in the synthesis, easily causes pollution to environment

Method used

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  • Method for synthesizing 5-trifluoro methyl-2'-desugarized uridine
  • Method for synthesizing 5-trifluoro methyl-2'-desugarized uridine
  • Method for synthesizing 5-trifluoro methyl-2'-desugarized uridine

Examples

Experimental program
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Effect test

Embodiment 1

[0016] Example 1 3', the preparation of 5'-diacetyl-2'-deoxyuridine (III)

[0017] 2'-deoxyuridine (1.03 g, 4.5 mmol), acetic anhydride (12 ml) and 4-N, N-dimethylaminopyridine (DMAP) (0.4 g) were added to the reaction flask, and the mixture was stirred at room temperature overnight . Concentrate to dryness under reduced pressure, add water to the obtained colorless solid, and filter to obtain 3',5'-diacetyl-2'-deoxyuridine product (1.23 g), yield 88%, mp108-109 ° C; [ α] D 25 15.5 (c1.2, CHCl 3 ).

[0018] 1 H NMR (δ, ppm, CDCl 3 ): 2.14 (s, 6, 3’ and 5’-COCH 3 ), 2.16-2.57(m, 2, H-2', H-2"), 4.35(m, 3, H-4', H-5', H-5"), 5.14-5.38(m, 1 , H-3'), 5.80(d, J=8.0Hz, 1, H-5), 6.30(d of d, J=8and 6Hz, 1, H-1'), 7.52(d, J=8.0Hz , 1, H-6).

Embodiment 2

[0019] Example 2 Preparation of 3', 5'-diacetyl-2'-deoxyuridine (III)

[0020] The preparation method is the same as in Example 1, wherein pyridine is used instead of 4-N, N-dimethylaminopyridine, and the reaction time is 2-3 days.

Embodiment 3

[0021] Example 3 Preparation of 5-iodo-3', 5'-diacetyl-2'-deoxyuridine (IV) 3', 5'-diacetyl-2'-deoxyuridine (0.5mmol), iodine (0.6 mmol), CAN (0.25 mmol) and acetonitrile (8 mL) was stirred at 80°C for one hour. Evaporate the solvent under reduced pressure, add saturated aqueous sodium chloride solution (10 ml) and a small amount of sodium bisulfite aqueous solution to the residue, extract three times with ethyl acetate (10 ml × 3), combine the organic phases, wash with water, and It was washed with aqueous solution (15 ml) and water (15 ml×2), and dried over anhydrous magnesium sulfate. After filtration, the filtrate was evaporated to dryness, and the crude product was purified by silica gel column chromatography or recrystallized from ethanol to obtain 201 mg of a colorless needle product with a melting point of 160.5-162°C.

[0022] 1 H NMR (δ, ppm, CDCl 3 ): 2.07, 2.11 (2s, 3 and 3, 3’ and 5’-COCH 3 ), 2.29-2.48(m, 2, H-2', H-2"), 4.20-4.29(m, 3, H-4', H-5', H-5"), 5.1...

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Abstract

The present invention relates to the synthesis process of 5-trifluoromethyl-2'-dexoy uridine. The compound is prepared with 2'-dexoy uridine as initial material and through iodizing, hydroxyl protection, trifluoromethylation and deprotection. The said process of the present invention has easy-to-obtain material, simple synthesis and no pollution.

Description

Technical field: [0001] The invention relates to the field of drug synthesis, in particular to a synthesis method of 5-trifluoromethyl-2'-deoxyuridine. Background technique: [0002] 5-Trifluoromethyl-2'-deoxyuridine (Trifluridine), also known as trifluridine or trifluorothymidine, is clinically used as an antiviral drug and is a thymidine analog that interferes with DNA synthesis, It is effective for primary keratoconjunctivitis and recurrent keratitis caused by herpes simplex virus types I and II. At the same time, it is an important intermediate for the preparation of the compound 5-trifluoromethyl-2', 3'-dideoxyuridine (5-trifluoromethyl-2'3'-dideoxyuridine) with high specificity against hepatitis B virus body. 5-trifluoromethyl-2', 3'-dideoxyuridine was developed by Bayer, and in Chinese patent application 92102448.7, a synthetic 5-trifluoromethyl-2', 3'-dideoxyuridine was disclosed The method of glucoside, it is starting raw material with ethyl trifluoropropionate, ...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/06
Inventor 杨炳辉邱金刚凌国昌
Owner FUBANG BIO PHARMA HANGZHOU
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