Cytidine, 5′-deoxy-5-fluoro-, 2′,3′-diacetate
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Cytidine, 5′-deoxy-5-fluoro-, 2′,3′-diacetate
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CAS No:
161599-46-8
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Formula:
C13H16FN3O6
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Chemical Name:
Cytidine, 5′-deoxy-5-fluoro-, 2′,3′-diacetate
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Synonyms:
Cytidine,5′-deoxy-5-fluoro-,2′,3′-diacetate;5′-Deoxy-2′,3′-di-O-acetyl-5-fluorocytidine;2′,3′-Di-O-acetyl-5′-deoxy-5-fluorocytidine;2′,3′-Di-O-acetyl-5′-deoxy-5-fluorocytidine
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CAS No:
Description
White to Off-White SolidChEBI: A member of the class of cytidines that is a metabolite of the drug capecitabine.
Cytidine, 5′-deoxy-5-fluoro-, 2′,3′-diacetate Basic Attributes
329.282
329.28
2017-001-1
Q6KTK8KQR2
DTXSID40167207
29389090
Characteristics
121
-0.7
1.57±0.1 g/cm3(Predicted)
81-83 °C
427.4±55.0 °C(Predicted)
212.3±31.5 °C
1.609
-20°C Freezer
Safety Information
24/25
P201, P202, P264, P273, P280, P281, P302+P352, P305+P351+P338, P308+P313, P321, P332+P313, P337+P313, P362, P391, P405, P501
H315
|Danger|H315 (33.33%): Causes skin irritation [Warning Skin corrosion/irritation]|P201, P202, P264, P273, P280, P281, P302+P352, P305+P351+P338, P308+P313, P321, P332+P313, P337+P313, P362, P391, P405, and P501|Aggregated GHS information provided by 7 companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
2',3'-di-O-acetyl-5'-deoxy-5-fluorocytidine has known transformation products that include Flucytosine.
Cytidine, 5′-deoxy-5-fluoro-, 2′,3′-diacetate Use and Manufacturing
5-Fluorocytosine (200.0 g, 1.55 mol) was suspended in 2 L of dichloromethane.1, 2, 3-Tri-O-acetyl-5-deoxyribose (403.0 g, 1.55 mol) was added at room temperature.Control temperature 10 to 20 C, Titanium tetrachloride (403.0 g, 1.55 mol) was added dropwise to a 1 L solution of dichloromethane under rapid stirring.After the completion of the dropwise addition, the reaction was continued at 10 to 20 C for 4 hours.Add sodium bicarbonate (781.0 g, 9.3 mol), Slowly add 100g of water, Stirring was continued for 3 hours after the completion of the dropping.After filtration, the filter cake was washed with dichloromethane (0.4 L×2), and the filtrate was washed once with saturated aqueous sodium hydrogencarbonate (2.0 L) and the organic phase was dried over anhydrous sodium sulfate (200 g) for 1 hour, filtered, and the filtrate was concentrated under reduced pressure to syrup.The residue was recrystallized from 2.0 L of isopropanol to afford 452 g of capecitabine intermediate as a white powder.The yield was 88.6%, the purity was 99.7%, and the maximum single impurity was 0.11%. The alpha-isomer was not detected.Figure 5 is a HPLC analysis of the capecitabine intermediate.Under nitrogen atmosphere, 1.80 kg of toluene, 125 g of compound of formula III, 2 g of ammonium sulfate and 247 g of HMDS were charged into the reaction vessel. After the addition was completed, the mixture was heated to reflux under warming and the mixture was refluxed for 3 hours. The solvent was concentrated under reduced pressure and the residue was dissolved with 1.40 Kg of CH2Cl2. 225 g of the compound of formula II was added and protected by nitrogen. The mixture was cooled to -5 C and 255 g of SnCl4 / 200 g of CH2Cl2 solution was added dropwise. Natural warming reaction to the point of disappearance of raw materials. Cool to about 5 , add 400g sodium bicarbonate, stirring, dropping 187.5g purified water, stirring at room temperature. Feed filtration, the filter cake was washed with 500g CH2Cl2 beating, drained. The filtrate was washed twice with 840 g of 5% aqueous sodium bicarbonate and once with 840 g of saturated brine and dried over anhydrous sodium sulfate. The desiccant was filtered off and the solvent was concentrated under reduced pressure to give a white solid. Add 500g of anhydrous ethanol to dissolve, filter, and dry to give a white solid (242.3g, 0.736mol, 83.6%), HPLC content of 98.39%.
A metabolite of Capecitabine.
Pharmaceuticals
Computed Properties
Molecular Weight:329.28
XLogP3:-0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:7
Rotatable Bond Count:5
Exact Mass:329.10231340
Monoisotopic Mass:329.10231340
Topological Polar Surface Area:121
Heavy Atom Count:23
Complexity:605
Defined Atom Stereocenter Count:4
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
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