Taurine → Taurolithocholic Acid

HRID 1721147

반응식

HRID 1721147 반응식
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]

참가 물질

8

반응물 4

HCID 1123TaurineHCID 8471TriethylamineHCID 31401Ursodeoxycholic AcidHCID 62493Pivaloyl chloride

생성물 1

HCID 439763Taurolithocholic Acid

시약·촉매·용매 3

HCID 14798Sodium Hydroxide용매HCID 312751,4-Dioxane용매HCID 21866353chloroform methanol HOAc용매

반응 조건

온도
10 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-619362136b74485a8c28abda93998860
출처 데이터셋
uspto-grants-1996_04
특허 번호
US05508453

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