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Lithium Hydroxide → Deoxycholic Acid

HRID 385172
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HRID 385172 반응식
[Li+].[OH-].C([O:6][C@@H:7]1[CH2:31][CH2:30][C@@:29]2([CH3:32])[C@H:9]([CH2:10][CH2:11][C@@H:12]3[C@@H:28]2[CH2:27][C@H:26]([OH:33])[C@@:25]2([CH3:34])[C@H:13]3[CH2:14][CH2:15][C@@H:16]2[C@H:17]([CH3:24])[CH2:18][CH2:19][C:20]([O:22]C)=[O:21])[CH2:8]1)(=O)C>O.C1COCC1.CO>[CH3:24][C@@H:17]([C@@H:16]1[C@@:25]2([CH3:34])[C@@H:26]([OH:33])[CH2:27][C@@H:28]3[C@@:29]4([CH3:32])[CH2:30][CH2:31][C@@H:7]([OH:6])[CH2:8][C@H:9]4[CH2:10][CH2:11][C@H:12]3[C@@H:13]2[CH2:14][CH2:15]1)[CH2:18][CH2:19][C:20]([OH:22])=[O:21]
참가 물질반응 조건실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 2

HCID 3939Lithium HydroxideHCID 11944640Methyl 3-acetyloxy-12-hydroxydeoxycholan-24-ate

생성물 1

HCID 222528Deoxycholic Acid수율 91.8%

시약·촉매·용매 3

HCID 887Methanol용매HCID 962Water용매HCID 8028Tetrahydrofuran
용매

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온도
50 °C

실험 절차

A solution of LiOH (187 mg, 4.4 mmol) in H2O (2.0 mL) was added to a solution of compound 2.1a (500 mg, 1.11 mmol) in THF (8 mL) and MeOH (8 mL). The resulting mixture was stirred for 3-4 h 50° C. Upon complete disappearance of the starting material by TLC, the reaction mixture was concentrated under vacuum. A mixture of water (10 mL) and 3 N HCl (1 mL) were combined and cooled to 0° C. and then added to the crude product. After stirring for 1 h at 0° C., the precipitated solids were filtered and then washed with water (10 mL) and hexane (20 mL). Drying under vacuum at room temperature provided deoxycholic acid (DCA, 400 mg, 91% yield) as a white solid.

후처리

  1. concentrationUpon complete disappearance of the starting material by TLC, the reaction mixture was concentrated under vacuum
  2. additionA mixture of water (10 mL) and 3 N HCl (1 mL)
  3. temperaturecooled to 0° C.
  4. additionadded to the crude product
  5. stirringAfter stirring for 1 h at 0° C.
  6. filtrationthe precipitated solids were filtered
  7. washwashed with water (10 mL) and hexane (20 mL)
  8. customDrying under vacuum at room temperature

출처 및 근거

ORD 기록
ord-fecebffaf3544226aaf62c7a0dbc2e1a
출처 데이터셋
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08367852B2

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