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CAS No. : | 862508-03-0 | MDL No. : | |
Formula : | C10H14FN3O3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 243.23 | Pubchem ID : | - |
Synonyms : |
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Signal Word: | Class: | ||
Precautionary Statements: | UN#: | ||
Hazard Statements: | Packing Group: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | Stage #1: Inert atmosphere Stage #2: With chloro-trimethyl-silane; 1,1,1,3,3,3-hexamethyl-disilazane In acetonitrile at 20℃; for 0.5 h; Stage #3: With trimethylsilyl trifluoromethanesulfonate In acetonitrile at -78 - 20℃; |
2',3'-Di-O-acetyl-5'-deoxy-5-fluoro-N4-(n-pentyloxycarbonyl)cytidine (11) A solution of 1,2,3-tri-O-acetyl-5-deoxy-D- ribofuranoside (107 mg, 0,41 mmol) in anhydrous acetonitrile (3 mL) was treated with N4-(n-pentyloxycarbonyl)-5-fluorocytosine (100 mg, 0,41 mmol) under an argon atmosphere. The resulting suspension was treated with hexamethyldisilazane anhydrous (87 μL, 0,41 mmol) and chlorotrimethylsilane (210 μL, 1,64 mmol). It was stirred at ambient temperature for 30 minutes. The reaction mixture was cooled at -78°C and trimethylsilyl triflate (87 μL, 0,49 mmol) was added. It was taken one more time to ambient temperature and it was stirred for 5 hours. It was diluted with dichloromethane (50 mL) and it was washed with water (2 x 20 mL). The organic phase was dried (Na2SO4) and the solvent was evaporated. The product was purified by means of column chromatography (silica gel). A mixture of hexane-ethyl acetate (4:1) was used as elution which gave 51 mg (28percent yield) of the desired product as a colorless oil. 1H RMN (CDCl3, 500 MHz) δ 0.91 (t, J = 7.1 Hz, 3H, H-5"), 1.36 (m, 4H, H-3", H-4"), 1.47 (d, J = 6.5 Hz, 3H, H-5'), 1.71 (p, J = 7.0 Hz, 2H, H-2"), 2.10 (s, 3H, COCH3), 2.11 (s, 3H, COCH3), 4.17 (t, J = 5.6 Hz, 2H, H-1 "), 5.01 (t, J = 5.5 Hz, 1H, H-), 5.30 (t, J = 5.4 Hz, 1H, H-) 5.95 (d, J = 4.2 Hz, 1H, H-1'), 7.42 (s, 1H, ), 12.01 (s, 1H); 13C RMN (CDCl3, 125 MHz) δ13.85, 18.60 (C-5'), 20.32 (COCH3), 20.43 (COCH3), 22.23 (C-4"), 27.85 (C-3"), 28.17 (C-2"), 66.59 (C-1"), 72.91, 73.88, 78.20, 87.96, 123.38, 123.65, 138.93, 146.18, 153.09, 153.25, 163.44, 169.56 (COCH3), 169.63 (COCH3). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
330.8 g | at 5 - 40℃; for 3 h; | (2) adding 201.6 g of 1,2,3-tri-O-acetyl-5-deoxy-6-ribofuranose to 1 of the step (1), 184g of boron trifluoride etherate was added dropwise at a temperature of 5 ° C to 10 ° C.complete, Warming up to 35 ° C -40 ° C for 3 h, then drip it back into 413.3g of sodium bicarbonate mixed with 153.3g of water, Stir the reaction for 2 h, The organic layer was dried by suction and concentrated. Use concentrate 50g methanol and 200g water mixture crystallization for 2h, suction filtration, drying to obtain capecitabine intermediate 2',3'-O-Diacetyl-5'-deoxy-5-fluoro-N4-[(pentyloxy)carbonyl]cytidine 330.8 g, total molar yield 96.3percent, product purity 99.65percent. Hydrogen The spectral data is the same as in the first embodiment. |