Thionyl Chloride → HCID 56846882, compound

Participants

Reaction Steps

To a solution of (3S,5R,8R,9S,10S,13R,14S,17R)-14-hydroxy-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)hexadecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-morpholinoethylcarbamate (43.7 mg, 0.08 mmol, 1 eq) in pyridine (3 mL) was added SOCl2 (57.1 mg, 0.48 mmol) at 0° C. The mixture was stirred at this temperature for about 2 h, quenched with saturated NaHCO3, and extracted with EtOAc. The organic layers were combined, dried with Na2SO4, concentrated and purified via Preparative TLC to afford (3S,5R,8R,9S,10S,13R,17S)-10,13-dimethyl-17-(2-oxo-2H-pyran-5-yl)-2,3,4,5,6,7,8,9,10,11,12,13,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-3-yl 2-morpholinoethylcarbamate (20 mg, 47.6%). LCMS (M+H+) m/z calculated 524.33. found 526.0. 1H NMR (CD3OD, 400 MHz) δ 7.64 (m, 2 H), 6.38 (m, 1 H), 5.37 (m, 1 H), 4.98 (m, 1 H), 3.78 (m, 4 H), 3.34 (m, 2H), 2.92 (m, 1 H), 2.90 (m, 7H), 2.50-1.30 (m, 18 H), 1.10(s, 3 H), 0.83 (s, 3 H).

Provenance & Evidence