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143157-24-8

1'-Epi 2',2'-Difluoro-2'-deoxyuridine 3',5'-Dibenzoate synthesis

2synthesis methods
-

Yield:95 % de

Reaction Conditions:

with tin(IV) chloride in 1,2-dichloro-ethane at 20 - 83; for 22 h;Product distribution / selectivity;

Steps:

2

A 0.46 g sample of l-acetyl-2-deoxy-3,5-dibenzoate-2,2-difluoro-ribofuranose(compound IV that can be obtained from commercially available material e.g. by method EPO > C T . - 8 ,1 S if, fi S: / ' H- H ' 3 & '9 reported in patent application WO2005095430) was dissolved in 15 ml of dichloroethane, and 1.26 g of 2,4-bis-O-trimethylsilyluracil and 0.89 ml Of SnCl4 were added at room temperature. The mixture was then heated to 83°C for 22 hours. The mixture was then allowed to cool to room temperature, and quenched via addition of 20 ml of a saturated sodium bicarbonate solution. The suspension was filtered over a pad of Celite eluting with 100 ml of dichloromethane. The filtrate was washed with 20 ml of saturated sodium bicarbonate solution, dried over Na2SO4, and filtered and concentrated under reduced pressure to obtain an off-white foam.[00047] The crude product, a 1 :5 mixture of anomers, was triturated in a 2: 1 heptane/ethyl acetate mixture, and filtered. The undissolved solid was identified (IH, 19F NMR, HPLC) as /3-anomer (95% de) of the title compound.1H NMR: δ (300 MHz, DMSO): 11.65 (IH, s); 8.10 (2H, d); 7.90 (2H, d); 7.80-7.42 (7H, m);6.37 (IH, t); 5.95-5.85 (IH, m); 5.77 (1, d); 4.92-4.85 (3H, m)

References:

WO2006/63105,2006,A1 Location in patent:Page/Page column 11-12