Acetic Acid → 2'-Deoxy-5-iodouridine 3',5'-diacetate

To 5-iodo-2′-deoxyuridine (2.1) (70.8 g, 200 mmol, 1 eq) in an 500 mL Erlenmeyer flask was added acetic acid (72 g, 68.7 mL, 1200 mmol, 6 eq) and acetic anhydride (51 g, 47.1 mL, 500 mmol, 2.5 eq). In a test tube at 0° C., the catalyst for the reaction was prepared by adding HClO4 (0.5 mL) over acetic anhydride (2 mL). Five drops of the catalyst were added into the Erlenmeyer flask at 0° C. with stirring. The reaction mixture was brought to room temperature and stirred for 4 hours where upon a thick white precipitate formed. The Erlenmeyer flask was filled with ether and stirred vigorously for 30 minutes. The white precipitate was filtered and the white cake was washed with ether (500 mL). The product was dried in the vacuum oven overnight to afford (2.2) (90.1 g, 95%) 1H-NMR (CDCl3) δ (ppm) 9.40 (bs, 1H, exchangeable, NH), 7.78 (s, 1H, H-6), 6.18 (dd, J=8.10 Hz, 1H, H-1′), 5.05 (m, 1H, H-3′), 4.07-4.25 (m, 3H, H-4′, 5′), 2.35 (m, 1H, H-2′b), 1.85-2.12 (m, 7H, 2×CH3, H-2′a)

1. customIn a test tube at 0° C., the catalyst for the reaction was prepared
2. customwas brought to room temperature
3. stirringstirred for 4 hours where upon a thick white precipitate
4. customformed
5. stirringstirred vigorously for 30 minutes
6. filtrationThe white precipitate was filtered
7. washthe white cake was washed with ether (500 mL)
8. customThe product was dried in the vacuum oven overnight

ORD record

ord-e59bba8c62ae48e7bc4fcde802c20e1f

Source dataset

uspto-grants-2002_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06444682B1