Chenodeoxycholic Acid → HCID 22809921, compound

HRID 1799448Notes

Reaction equation

HRID 1799448 reaction equation
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[CH2:13][CH2:14][C@@H:15]3[C@@:20]4([CH3:26])[CH2:21][CH2:22][C@@H:23]([OH:25])[CH2:24][C@H:19]4[CH2:18][C@@H:17]([OH:27])[C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6].[C:29](=O)(O)[O-].[Na+]>CO.Cl>[OH:25][C@@H:23]1[CH2:22][CH2:21][C@@:20]2([CH3:26])[CH:19]([CH2:18][C@@H:17]([OH:27])[C@@H:16]3[C@@H:15]2[CH2:14][CH2:13][C@@:12]2([CH3:28])[C@H:11]3[CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]([O:7][CH3:29])=[O:6])[CH2:24]1

Participants

5

Reactant 2

HCID 10133Chenodeoxycholic AcidHCID 516892Sodium Bicarbonate

Product 1

HCID 22809921HCID 22809921, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Conditions

Temperature
80 °C

Procedure

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.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 2.5 h
  3. temperaturecooled to room temperature
  4. customthe solvent was removed
  5. addition15 mL of water was added to the mixture
  6. extractionthe crude product was extracted with EtOAc (20 mL×3)
  7. dry with materialThe combined organic layers were dried over Na2SO4
  8. concentrationconcentrated
  9. customthe crude product was chromatographed (SiO2, gradient, hexane/EtOAc 1:2 to EtOAc only)
  10. customto give 1.08 g (2.64 mmol, >100%
  11. dry with materialless dry) of 25 as a white solid

Sources & evidence

ORD record
ord-cc288145f720489992ccc640c1d4da29
Source dataset
uspto-grants-2013_01
Patent number
US08344125B2

Reaction notes

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