Hydrochloric Acid → HCID 86605356, compound

Participants

Reaction Steps

A solution of 35 (52.2 g, 55.18 mmol) in acetonitrile (2 L) is treated with conc. HCl (4 mL) at room temperature and the mixture is stirred for 24 h. The reaction is neutralized with 2N NaOH and diluted with water (250 mL). It is then concentrated to remove most of acetonitrile and treated with ethyl acetate (500 mL) and water (200 mL). The organic layer is separated and dried over MgSO4. After filtration, the filtrate is concentrated and the residue is purified on a silica gel column using ethyl acetate:hexanes:methanol (1:1:0 to 1:1:0.2) as eluent to give 6.18 g (17%) of 36 as a white solid: 1H NMR (DMSO-d6): δ 8.27 (s, 1H), 7.93 (s, 1H), 7.38-7.20 (m, 13H), 6.89 (d, J=9.0 Hz, 2H), 4.92-4.80 (m, 1H), 4.64 (t, J=5.1 Hz, 1H), 4.50-4.36 (m, 2H), 4.14 (t, J=9.8 Hz, 1H), 3.89-3.65 (m, 3H), 3.76 (s, 3H), 3.42-3.18 (m, 2H), 2.22-1.95 (m, 2H), 1.18-1.11 (m, 6H), 1.06 (d, J=6.2 Hz, 6H). IR (KBr, cm−1) 3418, 2978, 1605, 1503 and 1250. Anal. Calcd for C36H44N5O6P.0.5 H2O: C, 63.33; H, 6.64; N, 10.26. Found: C, 63.31; H, 6.47; N, 10.19.

Provenance & Evidence