Purification of 2-iodo-6-chloro-9-beta(2',3',5'-trioxyacetyl-D-furanose)purine

A technology of trioxyacetyl and ribofuranose, applied in sugar derivatives, organic chemistry, etc., can solve the problems of long cycle, difficult operation of silica gel column chromatography, high cost, etc., and achieve short cycle, stable product quality and low cost Effect

Inactive Publication Date: 2009-05-06
SHANGHAI CHEM REAGENT RES INST
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0007] The technical problem that the present invention solves is to provide a kind of purification method of 2-iodo-6-chloro-9-β-(2', 3', 5'-trioxyacetyl-D-ribofuranose) purine, to overcome existing In the existing technology, the silica gel column chromatography is difficult to operate, the cycle is long, and the cost is high.

Method used

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  • Purification of 2-iodo-6-chloro-9-beta(2',3',5'-trioxyacetyl-D-furanose)purine

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Embodiment 1

[0021] 24mmol (10.24 g), iodine 12mmol (6.08g), cuprous iodide 12.6mmol (4.8g), diiodomethane 20ml, tetrahydrofuran 120ml, stirred at room temperature, then added 10ml of isoamyl nitrite to reflux, reacted for 45 minutes, and kept at 70°C , add 3 g of activated carbon (fineness 200-400 mesh), stir for 15 minutes, cool to room temperature, filter, add 500 ml of ethyl acetate to dissolve the filtrate after evaporating the solvent, wash with 100 ml of 10% sodium thiosulfate solution, and separate the organic phase , dried with anhydrous magnesium sulfate for 30 minutes, and the filtered filtrate was evaporated to dryness to obtain 14.2 g of crude product.

[0022] Add 14.2 g of the crude product to 60 ml of ethyl acetate, heat to 60°C, and after the crude product is completely dissolved, add 60 ml of n-hexane (the volume ratio of solvent ethyl acetate to n-hexane is 1:1), recrystallize, filter, and dry. Obtain 2-iodo-6-chloro-9-β-(2', 3', 5'-trioxyacetyl-D-ribofuranose) purine p...

Embodiment 2

[0024] With heating, stirring, add 2-amino-6-chloro-9-β-(2', 3', 5'-trioxyacetyl-D-ribofuranose) purine 30.6g ( 72mmol), iodine 18.3g (36mol), cuprous iodide 14.4g (37.8mmol), diiodomethane 60ml, tetrahydrofuran 360ml, stirred at room temperature, then added 30ml of isoamyl nitrite to reflux, reacted for 45 minutes, and kept at 70°C , add 6 g of activated carbon (fineness 200-400 mesh), stir for 45 minutes, cool to room temperature, filter, add ethyl acetate 1000 ml to dissolve after the filtrate evaporates the solvent, wash with 250 ml of 15% sodium thiosulfate solution, and separate the organic phase , dried with anhydrous magnesium sulfate for 30 minutes, and the filtered filtrate was evaporated to dryness to obtain 40.1 g of crude product.

[0025] Add 40.1 g of the crude product to 150 ml of ethyl acetate, heat to 60°C, and after the crude product is completely dissolved, add 225 ml of n-hexane (the volume ratio of solvent ethyl acetate to n-hexane is 1:1.5), recrystalliz...

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Abstract

Purification of 2-iodine-6-chlorine-9-beta-(2,,3,,5,-acetyl trioxide-D-ribofuranose) purine is carried out by dissolving 2-amino-6-chlorine-9-beta-(2,,3,,5,- acetyl trioxide-D-ribofuranose) purine, iodine, copper iodide and diiodomethane into butylenes oxide, reflux reacting with isoamyl nitrite, decolorizing by active carbon, and re-crystallizing by solvent with double component to obtain purified final product. Its advantages include low cost, short period, stable quality and controllable operation.

Description

technical field [0001] The invention relates to a method for purifying 2-iodo-6-chloro-9-β-(2',3',5'-trioxyacetyl-D-ribofuranose)purine. Background technique [0002] 2-iodo-6-chloro-9-β-(2',3',5'-trioxyacetyl-D-ribofuranose)purine is an important intermediate of natural nucleoside analogs with antibacterial activity, Its derivatives have strong anti-tumor activity and have broad application prospects in nucleoside drugs. [0003] Its structural formula is as follows: [0004] [0005] J.Med.Chem, 1992, Vol.35, No.2,242-252 reported 2-amino-6-chloro-9-β-(2', 3', 5'-trioxyacetyl-D-ribofuranose ) purine and iodine, cuprous iodide, and diiodomethane were dissolved in tetrahydrofuran, and carried out reflux reaction with isoamyl nitrite, evaporated to remove the solvent, moved into a silica gel chromatography column, rinsed with chloroform to no iodine color, and used 1 % ethanol-chloroform solution rinse, the collected eluate was evaporated to remove the solvent, and puri...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07H19/167
Inventor 廖本仁袁振文
Owner SHANGHAI CHEM REAGENT RES INST
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