Deoxycholic Acid → 12alpha-Hydroxy-3-oxo-5beta-cholan-24-oic Acid

HRID 463532

Reaktionsgleichung

Reaktionsgleichung von HRID 463532
[CH3:1][C@@H:2]([C@@H:8]1[C@@:12]2([CH3:28])[C@@H:13]([OH:27])[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][CH2:17][C@H:16]3[C@@H:11]2[CH2:10][CH2:9]1)[CH2:3][CH2:4][C:5]([OH:7])=[O:6]>C(Cl)(Cl)Cl.C(O)C>[OH:27][C@@H:13]1[C@@:12]2([CH3:28])[C@@H:11]([CH2:10][CH2:9][C@@H:8]2[C@H:2]([CH3:1])[CH2:3][CH2:4][C:5]([OH:7])=[O:6])[C@H:16]2[C@@H:15]([C@:20]3([CH3:26])[C@H:19]([CH2:18][CH2:17]2)[CH2:24][C:23](=[O:25])[CH2:22][CH2:21]3)[CH2:14]1

Komponenten

3

Edukt 1

HCID 222528Deoxycholic Acid

Produkt 1

HCID 16073812alpha-Hydroxy-3-oxo-5beta-cholan-24-oic AcidAusbeute 25,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21889567Chloroform ethanolLösungsmittel2×

Versuchsvorschrift

The above mixture of oxidation products of deoxycholic acid (310 mg) resulted from the eluate of chloroform-ethanol (97:3, v/v) was dissolved in a small amount of chloroform-ethanol (99:1, v/v) and the solution was absorbed on silica gel (20 g) column. The column was eluted with chloroform-ethanol (98:2, v/v) and then with chloroform-ethanol (97:3, v/v). Each 10 ml portions of the eluate was collected in a fraction tube. Fractions which showed a corresponding single spot by thin layer chromatography were combined and the solvent was distilled off by a rotary evaporator. As the results, 12α-hydroxy-3-keto-5β-cholanic acid (80 mg) was obtained from the first half of the fractions eluted with chloroform-ethanol (98:2, v/v) and 12α-hydroxy-3-keto-4-cholenic acid (10 mg) was obtained from the latter half thereof. 12α-Hydroxy-3-keto-5β-pregnan-20α-carboxylic acid (5 mg) was obtained from the first half of the fractions eluted with chloroform-ethanol (97:3, v/v) and 12α-hydroxy-3-keto-chola-1,4 -dienic acid (10 mg) was obtained from the latter half thereof.

Aufarbeitung

  1. customv/v) and the solution was absorbed on silica gel (20 g) column
  2. washThe column was eluted with chloroform-ethanol (98:2
  3. customEach 10 ml portions of the eluate was collected in a fraction tube
  4. distillationthe solvent was distilled off by a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-69030becfde94377ac2b52cf29dee9fe
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04520102

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