HCID 69486922, compound → HCID 9903844, compound

Participants

Reaction Steps

A solution of 20 (970 mg, 2.08 mmol) in methanolic ammonia (previously saturated at −10° C.) (50 mL) was stirred at room temperature overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between methylene chloride (100 ml) and water (100 ml). The aqueous layer was washed with methylene chloride (2×100 mL), and concentrated under reduced pressure. The residue was purified by silica gel column chromatography [eluent: stepwise gradient of methanol (10–30%) in ethyl acetate] to afford pure 21 (554 mg, 95%). Crystallization from methanol/ethyl acetate gave 21 as a white solid. Mp: 96–97 (dec.); 1H-NMR (DMSO-d6): δ 8.33 (s, 1H, H-2), 8.13 (s, 1H, H-8), 7.36 (brs, 2H, NH2), 5.84 (d, 1H, H-1′, J1′-2′=7.4 Hz), 5.69 (dd, 1H, OH-5′, J=4.2 Hz and J=7.8 Hz), 5.33 (d, 1H, OH-2′, J=6.6 Hz), 5.13 (d, 1H, OH-3′, J=4.4 Hz), 4.86 (m, 1H, H-2′), 4.04 (t, 1H, H-3′), 3.58–3.32 (m, 2H, H-5′ and H-5″), 1.15 (s, 3H, CH3); MS (matrix GT): FAB>0 m/z 563 (2M+H)+, 374 (M+G+H)+, 282 (M+H)+, 136 (B+2H)+, FAB<0 m/z 561 (2M−H)−, 280 (M−H)−, 134 (B)−.

Provenance & Evidence