Taurine → Taurolithocholic Acid

HRID 1721147

Reaction equation

HRID 1721147 reaction equation
C(N(CC)CC)C.[CH3:8][C@@H:9]([C@@H:15]1[C@@:19]2([CH3:35])[CH2:20][CH2:21][C@@H:22]3[C@@:27]4([CH3:33])[CH2:28][CH2:29][C@@H:30]([OH:32])[CH2:31][C@H:26]4[CH2:25][C@H:24](O)[C@H:23]3[C@@H:18]2[CH2:17][CH2:16]1)[CH2:10][CH2:11][C:12](O)=[O:13].C(Cl)(=O)C(C)(C)C.[NH2:43][CH2:44][CH2:45][S:46]([OH:49])(=[O:48])=[O:47]>O1CCOCC1.[OH-].[Na+].C(Cl)(Cl)Cl.CO.CC(O)=O>[CH3:8][C@@H:9]([C@@H:15]1[C@@:19]2([CH3:35])[CH2:20][CH2:21][C@@H:22]3[C@@:27]4([CH3:33])[CH2:28][CH2:29][C@@H:30]([OH:32])[CH2:31][C@H:26]4[CH2:25][CH2:24][C@H:23]3[C@@H:18]2[CH2:17][CH2:16]1)[CH2:10][CH2:11][C:12]([NH:43][CH2:44][CH2:45][S:46]([OH:49])(=[O:48])=[O:47])=[O:13]

Participants

8

Reactant 4

HCID 1123TaurineHCID 8471TriethylamineHCID 31401Ursodeoxycholic AcidHCID 62493Pivaloyl chloride

Product 1

HCID 439763Taurolithocholic Acid

Reagents, catalysts & solvents 3

HCID 14798Sodium HydroxideSolventHCID 312751,4-DioxaneSolventHCID 21866353chloroform methanol HOAcSolvent

Conditions

Temperature
10 °C

Procedure

2.5 g (24.75 mmol) of triethylamine are added dropwise at a temperature of 20° C. to a suspension of 9.6 g (24.45 mmol) of ursodeoxycholic acid in 60 ml of dioxane. Once solubilized, the mixture is cooled to 10° C., 2.98 g (24.70 mmol) of pivaloyl chloride are added slowly and the temperature is then allowed to rise spontaneously to 20° C. The salts formed are filtered off and the precipitate is washed with dioxane, the washings being added to the solution. 3.84 g (30.72 mmol) of taurine dissolved in 24 ml of 1N NaOH are added to the solution obtained and the mixture is stirred for 3 hours at 15° C. The reaction can be followed by thin layer chromatography using CHCl3 /MeOH/AcOH=70/30/5 as the eluent.

Workup

  1. customto rise spontaneously to 20° C
  2. customThe salts formed
  3. filtrationare filtered off
  4. washthe precipitate is washed with dioxane
  5. additionthe washings being added to the solution
  6. additionare added to the solution
  7. customobtained
  8. customThe reaction

Sources & evidence

ORD record
ord-619362136b74485a8c28abda93998860
Source dataset
uspto-grants-1996_04
Patent number
US05508453

Linked notes

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