Dimethylformamide → HCID 178486368, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of nucleoside 6.6 (10 mg, 0.030 mmol) in DMF (0.5 mL) was added N-bromosuccinimide (11.25 mg, 2.10 eq.) at 0° C. under argon. The reaction mixture was stirred at 0° C. for 1 hr then quenched with MeOH (0.5 mL). The mixture was evaporated to dryness and the residue was purified on a silica gel column with 5% MeOH in CH2Cl2 to give compound 14.1 as a mixture of diastereoisomers (8 mg, 65%). The isolated compound was characterized by 1H NMR, COSY, NOESY and LCMS. 1H NMR (300 MHz, DMSO-d6) δ 11.29 (s, 1H, NH), 8.54 (s, 1H, H-4), 8.00 (s, 1H, H-1), 6.24, 6.21 (2s, 1H, H-1′), 5.22-5.08 (m, 4H, 3×OH, H-8), 4.77-4.73 (m, 1H, H-9), 3.95-3.7 (m, 4H, H-3′, H-4′ 2×H-5′), 3.24, 3.21 (2s, 3H, OCH3), 0.68, 0.66 (2s, 3H, CH3). ES MS: 501.7 (M+CH3COO−).

Provenance & Evidence