Ammonia → HCID 510972, compound

Participants

Reaction Steps

Compound 11 (890 mg, 1.93 mmol) was treated with methanolic ammonia (previously saturated at −10° C.), (12 mL) at 100° C. in a stainless-steel bomb for 3 hours, then cooled to room temperature. The solvent was evaporated under reduced pressure and the residue was partitioned between methylene chloride (40 mL) and water (40 mL). The aqueous layer was washed with methylene chloride (2×40 mL), concentrated under reduced pressure. The crude material was purified by silica gel column chromatography [eluent: methylene chloride/methanol/ammonium hydroxide 65:30:5]. The collected fractions were evaporated under reduced pressure and in absolute ethanol (6.3 mL). To the solution was added a 2N hydrochloric acid solution (1.5 mL) and the mixture was stirred before being concentrated under reduced pressure. The procedure was repeated twice and 12 was precipitated from absolute ethanol. Mp: 213–214 (dec.); UV (methanol): λmax=280 nm (ε=9800), λmin=245 nm (ε=3600); 1H-NMR (DMSO-d6): δ 9.82 (s, 1H, NH2), 8.72 (s, 1H, NH2), 8.34 (d, 1H, H-6, J6-5=7.8 Hz), 6.21 (d, 1H, H-5, J5-6=7.8 Hz), 5.83 (d, 1H, H-1′, J1′-2′=5.8 Hz), 4.22 (d, 1H, OH-2′, JOH-2′=6.5 Hz), 5.6–4.7 (m, 3H, OH-2′, OH-3′ and OH-5′), 4.28 (t, 1H, H-2′, J=5.6 Hz), 3.99 (d, 1H, H-3′, J=5.3 Hz), 3.43 (m, 2H, H-5′ and H-5″), 1.14 (s, 3H, CH3); MS (matrix GT): FAB>0 m/z 515 (2M+H)+, 258 (M+H)+, 147 (S)+, 112 (BH2)+ FAB<0 m/z 256 (M−H)−.

Provenance & Evidence