Method for separating emtricitabine

A technology of emtricitabine and separation method, which is applied in the field of chemical processing, can solve problems such as poor product quality and salicylic acid residue, and achieve the effects of simple technology, reduced pollution, and safe and reliable operation

A technology of emtricitabine and separation method, which is applied in the field of chemical processing, can solve problems such as poor product quality and salicylic acid residue, and achieve the effects of simple technology, reduced pollution, and safe and reliable operation

CN101671333AActive Publication Date: 2010-03-17CANGZHOU SENARY CHEM SCI TEC
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  • Method for separating emtricitabine
  • Method for separating emtricitabine

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0025] Concentrate the reaction filtrate containing about 4g of emtricitabine to dryness, dissolve it in 30ml of methanol, add 20g of resin, add 210ml of dichloromethane, and stir for 15min; heat to reflux for 7h, cool to room temperature, filter, wash with methanol, and dry to constant weight. Pour the dried polymer resin into a round bottom flask, add 30ml of methanol, 210ml of dichloromethane, and 2ml of triethylamine, heat to reflux for 7h, filter, wash with methanol, evaporate the filtrate to dryness, and weigh 2.54g. Yield 63.5%.

Embodiment 2

[0027] Concentrate the reaction filtrate containing about 4 g of emtricitabine to dryness, dissolve it in 250 ml of methanol, add 20 g of resin, and stir for 15 min; heat to reflux for 7 h, cool to room temperature, filter, wash with methanol, and dry to constant weight. Pour the dried polymer resin into a round bottom flask, add 30ml of methanol, 210ml of dichloromethane, and 2ml of triethylamine, heat to reflux for 7h, filter, wash with methanol, evaporate the filtrate to dryness, and weigh 1.73g. Yield 43.2%.

Embodiment 3

[0029] Concentrate the reaction filtrate containing about 4 g of emtricitabine to dryness, dissolve it in 30 ml of methanol, add 20 g of resin, add 210 ml of dichloromethane, and stir for 15 min; after stirring at 40°C for 7 h, cool to room temperature, filter, and wash with methanol. Dry to constant weight. Pour the dried polymer resin into a round bottom flask, add 30ml of methanol, 210ml of dichloromethane, and 2ml of triethylamine, heat to reflux for 7h, filter, wash with methanol, evaporate the filtrate to dryness, and weigh 1.93g. Yield 48.2%.

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Abstract

The invention discloses a method for separating emtricitabine. Salicylic acid chloromethylate and polystyreneresin are adopted to have Friedel-Crafts alkylation reaction under the catalysis of aluminium trichloride to obtain salicylic acid functionalized polystyreneresin; salicylic acid functionalized polystyreneresin and the reaction mixture of synthetic emtricitabin are heated together, the emtricitabin in the mixture is complexed with the salicylic acid on the resin, the resin combined with the emtricitabine is separated by filtering, and then emtricitabine is analyzed with triethylamine; and the used resin is processed into regenerated resin with hydrochloric acid 1mol / L and reused again. The invention has the advantages of safe and reliable operation and simple and easy operation, andis suitable for mass production; and the resin can be reused after regeneration so as to reduce the production cost and also reduce the pollution to the environment.

Description

technical field [0001] The invention belongs to a chemical treatment method, in particular to a separation and purification method of emtricitabine. Background technique [0002] Emtricitabine (emtricitabine), the chemical name is 4-amino-5-fluoro-1-[(2R,5S)-2-hydroxymethyl-1,3-oxathiolan-5-yl]-2 (1H)-pyrimidinone. It is a new type of nucleoside reverse transcriptase inhibitor, which has antiviral activity against HlV-1, HlV-2 and HBV. In July 2003, the US FDA approved Gilead Sciences' once-a-day nucleoside reverse transcriptase inhibitors. Emtricitabine is used in combination with other antiretroviral drugs to treat HIV infection in adults. During the synthesis of emtricitabine, many times of recrystallization or column chromatography separation and purification are used (Bertolini G, et al. WO, 2004085432. Ran Dongsheng. CN, 1563002. Gong Pingping. Chinese Journal of Medicinal Chemistry, 2002, 12(1):34~36). These methods are not suitable for mass production of emtrici...

Claims

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Application Information

Patent Timeline
17 Mar 2010
Publication
CN101671333A
IPC
C07D411/04
Inventors
赵继全; 张月成