HCID 86693883, compound → HCID 71664659, compound

Participants

Reaction Steps

Compound 28 (0.2 g, 0.32 mmol) was dissolved in saturated MeOH with NH3 (20 mL) and stirred for 8 h at room temperature. The solvent was evaporated under vacuum and the residue was purified by silica gel vacuum column (35% EtOAc/hexane) to give the debenzolated compound. Debenzoylated compound was dissolved in 10 mL of CF3COOH/H2O (2:1, v/v) and heated to 50° C. for 3 h. The solvent was removed under vacuum and the residue was co-evaporated with ethanol (3×10 mL) under vacuum. The residue was purified by combiflash chromatography (7% MeOH/CH2Cl2) to give 29 in 60 mg (68%) as white foam. [α]24D 5.4° (c 0.67, MeOH); 1H NMR (500 MHz, DMSO-d6) δ 11.17 (bs, 1 H), 7.68 (d, J=15.6, 1 H), 5.80 (d, J=19.7, 1H), 5.67 (d, J=14.5 Hz, 1 H), 4.74-4.78 (bs, 2 H, —OH), 4.70 (m, 1H), 4.10-4.13 (bm, 1 H, —OH), 3.32-3.43 (m, 2 H), 2.1-2.08 (m, 1 H), 0.69-0.74 (m, 1 H), 0.49-0.56 (m, 2 H), 0.43 (m, 1 H); 13C NMR (500 MHz, MeOH-d4) δ 164.9, 161.4, 152.3, 140.2, 109.6, 76.0, 74.0, 60.2, 51.4, 21.1, 14.7, 11.0, 7.3; HR-MS Cald. For (C12H15FN2O4+H)+ 270.16, found 270.1226.

Provenance & Evidence