Chenodeoxycholic Acid → Ursodeoxycholic Acid

HRID 1153703

Reaktionsgleichung

Reaktionsgleichung von HRID 1153703
[K].CCSC(N(CC(C)C)CC(C)C)=O.[OH:16][C@@H:17]1[CH2:40][CH2:39][C@@:38]2([CH3:41])[C@H:19]([CH2:20][C:21](=[O:43])[C@@H:22]3[C@@H:37]2[CH2:36][CH2:35][C@@:34]2([CH3:42])[C@H:23]3[CH2:24][CH2:25][C@@H:26]2[C@H:27]([CH3:33])[CH2:28][CH2:29][C:30]([OH:32])=[O:31])[CH2:18]1.[Na].C[C@@H]([C@@H]1[C@@]2(C)CC[C@@H]3[C@@]4(C)CC[C@@H](O)C[C@H]4C[C@@H](O)[C@H]3[C@@H]2CC1)CCC(O)=O>C(O)CCC>[CH3:33][C@@H:27]([C@@H:26]1[C@@:34]2([CH3:42])[CH2:35][CH2:36][C@@H:37]3[C@@:38]4([CH3:41])[CH2:39][CH2:40][C@@H:17]([OH:16])[CH2:18][C@H:19]4[CH2:20][C@H:21]([OH:43])[C@H:22]3[C@@H:23]2[CH2:24][CH2:25]1)[CH2:28][CH2:29][C:30]([OH:32])=[O:31]

Komponenten

7

Edukt 5

HCID 10133Chenodeoxycholic AcidHCID 16181ButylateHCID 4442627-Ketolithocholic acidHCID 5360545SodiumHCID 5462222Potassium

Produkt 1

HCID 31401Ursodeoxycholic Acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

To a solution of potassium ter.butylate (3.77 g, 33.6 mmols) and 3alpha-hydroxy-7-keto-5beta-cholanic acid (2.5 g, 6.36 mmols) in ter.butyl-alcohol (50 ml), kept at the reflux under nitrogen and under stirring, sodium metal (1.75 g, 0.76 gram-atoms) is added. The reaction mixture is maintained under stirring and reflux for 2 hours and then worked up as disclosed in example 1; 2.5 g of the residue consisting of the CDCA (7%) and the UDCA (93) are thus obtained.

Aufarbeitung

  1. temperaturereflux under nitrogen
  2. temperatureThe reaction mixture is maintained
  3. stirringunder stirring
  4. temperaturereflux for 2 hours

Quellen und Nachweise

ORD-Eintrag
ord-2cdeffde71194bd597deab82f1c1249f
Quelldatensatz
uspto-grants-1984_12
Patentnummer
US04486352

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