Chenodeoxycholic Acid → HCID 22809921, compound

Participants

Reaction Conditions

Reaction Steps

CDCA (1.00 g, 2.50 mmol) was dissolved in methanol (43 mL), refluxed at 80° C., and then 12 drops of conc. hydrochloric acid (HCl) was added to this solution. The reaction mixture was heated at reflux for 2.5 h, cooled to room temperature, neutralized with a saturated solution of sodium bicarbonate, and the solvent was removed. 15 mL of water was added to the mixture, and the crude product was extracted with EtOAc (20 mL×3). The combined organic layers were dried over Na2SO4, concentrated, and the crude product was chromatographed (SiO2, gradient, hexane/EtOAc 1:2 to EtOAc only) to give 1.08 g (2.64 mmol, >100%, less dry) of 25 as a white solid. Rf 0.40 (EtOAc); 1H NMR (400 MHz, CDCl3) 3.80 (m, 1H, H-3/H-7), 3.63 (s, 3H, CO2CH3), 3.40 (m, 1H, H-3/H-7), 2.35-0.93 (m, 28H), 0.89 (d, 3H, J=6.5 Hz, CH3), 0.87 (s, 3H, CH3), 0.62 (s, 3H, CH3); MS (ESI) Calcd for C25H42O4Na (M+Na+): 429.3. Found: 429.3.

Provenance & Evidence