HCID 53722258, compound → HCID 53834200, compound

Participants

Reaction Steps

A solution of 0.176 g (0.359 mmole) of 89 in 10 mL of NH3 /MeOH was stirred in a pressure bottle at room temperature for 5 hr. The reaction mixture was evaporated and coevaporated with MeOH (3×, bath temperature <40° C.), The resulting solid was recrystallized from MeOH to give 0.097 g (2 crops, 74%) of 90 as white crystals. MP 152°-153° C. MS (El) m/e 361.9685 (10%, M+ =361.9669). 1H NMR (DMSO-d6): d 8.43 (d, 1, 7-H, J7-5 =2.0 Hz), 7.59 (d, 1, 4-H, J4-5 =8.5 Hz), 7.43 (dd, 1, 5-H), 5.88 (d, 1, 1'-H, J1'-2' =8.0 Hz), 5.49 (d, 1, 2'-OH, J2'-2'OH =6.5 Hz), 5.34 (t, 1, 5'-OH, J5'-5'OH =4.5 Hz), 5.27 (d, 1, 3'-OH, J3'-3'OH 4.5 Hz), 4.45 (m, 1, 2'-H, J2'-3' =5.5 Hz), 4.14, (m, 1, 3'-H, J3'-4' =2.0 Hz), 4.00 (m, 1, 4'-H, J4'-5' =J4-5" =3.5 Hz), 3.70 (m, 2, 5'-H and 5"-H, J5'-5" =12.0 Hz). 13C NMR (DMSO-d6): d 140.70 (C2), 140.49 (C3a), 134.02 (C7a), 125.95 (C5), 120.46 (C4), 116.01 (C7), 115.87 (C6), 88.99 (C1'), 86.32 (C4'), 71.40 (C2'), 69.79 (C3'), 61.15 (C5').

Provenance & Evidence