Acetone → HCID 10928796, compound

Participants

Reaction Steps

Hydrazine hydrate (2.80 mL, 57.4 mmol) was added to a solution of 1-(2-O-acetyl-3,5-di-O-benzoyl-β-L-xylofuranosyl)-5-fluorouracil 2 (9.80 g, 19.1 mmol) in acetic acid (35 mL) and pyridine (150 mL). The resulting solution was stirred overnight at room temperature. Acetone (50 mL) was added and the mixture was stirred during 2 h. The reaction mixture was concentrated to a small volume and partitioned between ethyl acetate (200 mL) and water (200 mL). Layers were separated and the organic phase was washed with a saturated aqueous sodium hydrogen carbonate solution (2×200 mL), and finally with water (2×200 mL). The organic phase was dried over sodium sulphate, then evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (0-5%) in methylene chloride] to give pure 3 (7.82 g, 87%), which was crystallized from methylene chloride; mp=93-97° C.; UV (ethanol): λmax=227 nm (ε=22800) 267 nm (ε=8200), λmin=249 nm (ε=5900); 1H-NMR (DMSO-d6): δ11.9 (br s, 1H, NH), 8.06 (d, 1H, H-6, J6-F5=6.9 Hz), 8.0-7.4 (m, 10H, 2 C6H5CO), 6.35 (d, 1H, OH-2′, JOH-2′=3.8 Hz), 5.77 (d, 1H, H-1′, J1′-2′=3.3 Hz), 5.43 (dd, 1H, H-3′, J3′-2′=3.1 Hz and J3′-4′=1.9 Hz) 4.8-4.6 (m, 3H, H-4′, H-5′ and H-5″), 4.43 (t, 1H H-2′, J=2.3 Hz); MS: FAB>0 (matrix GT) m/z 941 (2M+H)+, 471 (M+H)+, 341 (S)+, 131 (BH2)+, 105 (C6H5CO)+; FAB<0 (matrix GT) m/z 939 (2M−H)−, 469 (M−H)−, 129 (B)−, 121 (C6H5CO2); [α]D20=−110 (c, 1.55 DMSO).

Provenance & Evidence