4-((2S)-3-Amino-2-hydroxy-propoxy)-phenol → 5-(4-{4-[(2S)-2-Hydroxy-3-(4-hydroxy-phenoxy)-propylamino]-piperidin-1-yl}-benzyl)-thiazolidine-2,4-dione

Participants

Reaction Steps

The title compound was prepared from 5-[4-(4-oxo-piperidin-1-yl)-benzyl]-thiazolidine-2,4-dione (which was obtained in Example 38) and 4-[(2S)-3-amino-2-hydroxy-propoxy]-phenol (which was obtained in Example 5) according to the procedure of Example 73 as a pale yellowish solid; mp>160° C. (decomposed); 1H NMR (300 MHz, DMSO-d6) δ 1.35–1.60 (m, 2 H), 1.85–2.05 (m, 2 H), 2.60–3.50 (m, 7 H), 3.67 (brd, J=12.1 Hz, 2 H), 3.75–3.95 (m, 3 H), 4.57 (dd, J=9.6, 3.8 Hz, 1 H), 6.66 (d, J=8.9 Hz, 2 H), 6.77 (d, J=8.9 Hz, 2 H), 6.85 (d, J=8.6 Hz, 2 H), 7.03 (d, J=8.6 Hz, 2 H), 8.92(brs, 1 H); MS (ES) m/z: 472.0 (MH+); HRMS Calcd. for C24H30N3O5S (MH+): 472.1906. Found 472.1898.

Provenance & Evidence