Thionyl Chloride → HCID 56846769, 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-(pyrrolidin-1-yl)ethylcarbamate (54 mg, 0.1 mmol, 1 eq) in pyridine (3 mL) was added SOCl2(71.4 mg, 0.6 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-(pyrrolidin-1-yl)ethylcarbamate (40 mg, 78.7%). LCMS (M+H+) m/z calculated 508.33. found 509.4. 1H NMR (CD3OD, 400 MHz) δ 7.63 (m, 2 H), 6.38 (m, 1 H), 5.36 (m, 1 H), 5.00 (m, 1 H), 3.38 (m, 2 H), 3.10 (m, 6 H), 2.90 (m, 1H), 2.60 (m, 1 H), 2.50 (m, 1 H), 2.30-1.30 (m, 21 H), 1.10(s, 3 H), 0.86 (s, 3 H).

Provenance & Evidence