Ethanol → HCID 11442092, compound

Participants

Reaction Steps

To a solution of 38 (0.050 g, 0.084 mmol) in CH2Cl2 (2 mL) was added EtOH (0.050 g, 1.08 mmol) and Et3N (0.016 g, 0.16 mmol). The mixture was stirred at ambient temperature for 18 h, diluted with CH2Cl2, washed with water and 0.1 N hydrochloric acid, dried (Na2SO4), and concentrated. The residue was separated by preparative RP-HPLC (C-18 Luna column, 85% MeCN/H2O/0.1% TFA) and the corresponding fractions were concentrated. The residue was dissolved in CH2Cl2 (0.3 mL) and cooled to 0° C. TFA (0.3 mL) was added and the mixture stirred at 0° C. for 1 h. The solvent was evaporated and co-evaporated with CH2Cl2 (2×10 mL) and the residue crystallized from a small amount of EtOAC to provide 37 (0.010 g) as an off-white solid; mp 135-136° C.; 1HNMR (DMSO-d6): δ 0.85 (t, J=7.2 Hz, 3H), 1.21 (t, J=7.2 Hz, 3H), 2.39 (q, J=7.2 Hz, 2H), 4.15 (q, J=7.2 Hz, 2H), 6.5 (d, J=16 Hz, 1H), 6.85 (d, J=9 Hz, 2H), 6.89 (d, J=9 Hz, 2H), 7.08-7.22 (m, 5H), 7.24 (d, J=7.9 Hz, 2H), 7.58 (d, J=16 Hz, 1H), 7.69 (d, J=7.9 Hz, 2H), 12.45 (br s, 1H); MS, m/z 465 (M+Na)+; Anal. calculated for C28H26O5.0.13H2O: C, 75.60; H, 5.95; Found: C, 75.61; H, 5.93.

Provenance & Evidence