HCID 86689286, compound → HCID 71621465, compound

Participants

Reaction Steps

A solution of 58a (3.5 g, 0.0093 mol) in AcOH (50 mL) was heated at 100° C. for 1 hr. The reaction mixture was concentrated in vacuo, and to the residue was added CH2Cl2 (100 mL) and 37% aqueous ammonia (15 mL). The organic phase was washed with saturated NaHCO3 (2×75 mL) and brine (1×75 mL), filtered through phase separation filter paper, and concentrated in vacuo to give 3.0 g of a pink solid. The solid was chromatographed on 50 g of silica gel with 10 g anhydrous sodium sulfate on top packed with hexanes. The column was eluted with 25 mL portions of hexanes for fractions 1-4, 25% EtOAc in hexanes for fractions 5-8, and 35% EtOAc in hexanes for fractions 9-20. The product eluted in fractions 11-20 to give 2.5 g (70%) of Compound #7 as a tan solid. HPLC analysis showed a purity of 97%. 1H NMR (300 MHz, CDCl3): δ 7.7 (d, 1H), 7.3-6.8 (m, 6H), 5.35 (s, 2H), 4.1 (m, 4H), 2.3 (m, 1H), 1.45 (t, 3H), 1.0 (d, 6H) ppm.

Provenance & Evidence