HCID 86689288, compound → HCID 71620984, compound

Participants

Reaction Steps

A solution of 60 (3.0 g, 0.0088 mol) in AcOH (50 mL) was heated at 100° C. for 3 hr. The mixture was then concentrated in vacuo. To the residue was added EtOAc (100 mL) and 37% aqueous ammonia (15 mL). The organic phase was washed with saturated NaHCO3 (2×75 mL) and brine (75 mL), filtered through phase separation filter paper, and concentrated in vacuo to give 3.0 g of a red oil. The oil was chromatographed on 30 g of silica gel with 10 g of anhydrous sodium sulfate on top packed with hexanes. The column was eluted with 25 mL portions of 10% CH2Cl2 in hexanes for fractions 1-4, 10% EtOAc in hexanes for fractions 5-8, 15% EtOAc in hexanes for fractions 9-12, 20% EtOAc in hexanes for fractions 13-16, 25% EtOAc in hexanes for fractions 17-20, 30% EtOAc in hexanes for fractions 21-24 and 35% EtOAc in hexanes for fractions 25-28. The product was eluted in fractions 21-27 to give 0.7 g (25%) of compound #9 as a brown oil. HPLC analysis showed a purity of 96%. 1H NMR (300 MHz, CDCl3): δ 7.65 (d, 1H), 7.3 (m, 2H), 6.95-6.75 (m, 5H), 4.7 (brs, 1H), 4.5 (s, 2H), 4.1 (q, 2H), 3.95 (d, 2H), 2.3 (m, 1H), 1.5 (t, 3H), 1.0 (d, 6H) ppm.

Provenance & Evidence