Sodium ethoxide → HCID 54008737, compound

To a stirred solution of ethyl 2-(2',3',5'-tri-O-benzoyl-β-D-ribofuranosyl)thiazole-4-carboxylate 8 (3.01 g, 5.00 mmol) in dry ethanol (50 ml) under argon atmosphere was added NaOEt (1.02 g, 15 mmol) powder. The reaction mixture was stirred at room temperature overnight, neutralized with Dowex 50W-X8 H+ resin and filtere. The resin was washed with ethanol (20 ml) and the filtrate evaporated to dryness. The residue was dissolved in salt free water (50 ml) and washed with CHCl3 (2×50 ml). The water extract was evaporated to dryness under reduced pressure to an oil. The oil was dissolved in minimum amount of warm ethyl acetate (10 mL). The solution was seeded with authentic 5 and once crystallization had begun the mixture was refrigerated (5° C.) for 16 h. The solid was collected by filtration, washed with cold (5° C.) ethyl acetate (5 mL), and dried (40° C., 1 mm); 1.2 g (83%), mp 74-78° C. 1H NMR (DMSO-d6): d 1.31 (t, 3H), 3.46-3.64 (m, 2H), 3.8-4.12 (m, 3H), 4.30 (q, 2H), 4.84 (t, 1H) 4.94 (d, 1H), 5.04 (d, 1H), 5.4 (d,1H) and 8.49 (s,1H).

1. washThe resin was washed with ethanol (20 ml)
2. customthe filtrate evaporated to dryness
3. dissolutionThe residue was dissolved in salt free water (50 ml)
4. washwashed with CHCl3 (2×50 ml)
5. extractionThe water extract
6. customwas evaporated to dryness under reduced pressure to an oil
7. dissolutionThe oil was dissolved in minimum amount of warm ethyl acetate (10 mL)
8. customThe solution was seeded with authentic 5 and once crystallization
9. custom(5° C.)
10. customfor 16 h
11. filtrationThe solid was collected by filtration
12. washwashed with cold (5° C.) ethyl acetate (5 mL)
13. customdried (40° C., 1 mm)

ORD record

ord-45eb60ee7f7543328e7c42cd434f3a9f

Source dataset

uspto-grants-1999_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05907036