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Methylene dichloride (120 mL) was taken in a 500 mL 4-necked RB flask fitted with magnetic bar, thermo pocket, guard tube and nitrogen inlet. 5'-Deoxy-5-fluoro-N4-(2-methyl-1-butyloxycarbonyl)-cytidine (4 g, 0.0114 mol) was added in one lot, once the clear solution was formed, CDI (2.257 g, 0.01393 mol) was added in one lot under nitrogen atmosphere and the reaction mixture was stirred over 10-12 h. After the completion of the reaction (TLC), the reaction mixture was filtered and washed with 2 volumes (20 mL) of methylene dichloride. Thus obtained crude product was further purified by column chromatography (1:1 hexane/EtOAc) to get the title compound. The desired product was isolated and concentrated in rota evaporator. Finally it is dried under vacuum at 50 C to get the pure product.
With sodium hydroxide; In acetone; at -15 - 10℃; for 2.0h;
General procedure: To a solution of K2CO3 (0.626 g, 0.0453 mol) in acetone (80 mL) was added 2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine (14 g, 0.0425 mol) in a 500 mL 4-necked RB flask fitted with magnetic bar, thermo pocket, guard tube and nitrogen inlet and stirred for 10-15 min 2-Methyl-1-butyl chloroformate first half (2.279 g, 0.0151 mol) was added through additional funnel over a period of 15-20 min at room temperature and continued to stirred for 3 h. After completion of 3 h, second half of 3-methyl-1-butyl chloroformate (1.129 g, 0.0075 mol) added at 25-30 C, progress of the reaction was monitored by TLC (ethylacetate: hexane 1:1). After completion of the reaction, the mixture was filtered and washed with 2 volumes (50 mL) of acetone. To the acetone layer 4 volumes of 10% NaOH solution added at -10 to -15 C over 2 h. After completion of the reaction indicated by TLC, the pH of the reaction mixture adjusted to 6.0 by using concentrated HCl. The acetone was distilled off completely by using rota evaporator. Thus obtained aqueous layer extracted with ethyl acetate 5 volumes (50 mL) and ethyl acetate layer reduced to 1 volume stirred for 30 min then 5 volumes of tertiary methyl butyl ether (TBME) (50 mL) was added, the obtained precipitate was stirred for 1 h at 20-25 C and 2 h at 0-5 C filtered off washed with 9:1 volumes of TBME and ethyl acetate and suck dried to obtained the crude product and it was further purified by column chromatography (1:1 hexane/EtOAc) to get the title compound.
10 g
With sodium hydroxide; at -15℃; for 0.5h;pH Ca. 12;
(c) cooling the reaction solution of the compound 3 to -15 C,Slowly add 10% sodium hydroxide solution (100 mL).Adjust the pH to around 12,The temperature is maintained at a low temperature for 30 minutes.TLC monitors the reaction completely;Adjust the reaction solution to neutral with concentrated hydrochloric acid.Spin dry acetone,The aqueous phase was extracted 3 times with ethyl acetate.The combined organic phases were dried over anhydrous sodium sulfate.Spin dry,Column chromatography gave 10 g of compound 1 (ie, capecitabine impurity F, CAS 910129-15-6; its nuclear magnetic spectrum is shown in Figure 2;Purity 99.9%).
11 g
With water; sodium hydroxide; at -15℃; for 0.5h;pH Ca. 12;
(c) Cooling the reaction solution of the compound 3 to -15 C, slowly add 10% sodium hydroxide solution (100 mL), adjust the pH to about 12, maintain the temperature at low temperature for 30 minutes, and monitor the reaction by TLC; The reaction mixture was adjusted to neutral with concentrated hydrochloric acid, and then evaporated to dryness. Column chromatography gave 11.0 g of compound 1 (ie, capecitabine impurity F, CAS 910129-15-6; its nuclear magnetic spectrum is shown in Figure 2; purity 99.9%).
11.8 g
With water; sodium hydroxide; at -15℃; for 0.5h;pH Ca. 12;
(c) cooling the reaction solution of the compound 3 to -15 C,Slowly add 10% sodium hydroxide solution (100 mL).Adjust the pH to around 12,The temperature is maintained at a low temperature for 30 minutes.TLC monitors the reaction completely;Adjust the reaction solution to neutral with concentrated hydrochloric acid.The acetone was spun and the aqueous phase was extracted with ethyl acetate three times.Column chromatography gave 11.8 g of compound 1(ie, capecitabine impurity F, CAS 910129-15-6; its nuclear magnetic spectrum is shown in Figure 2; purity 99.9%).
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