p-Toluenesulfonic acid → 3alpha,7beta-Ditetrahydropyranyloxy-5beta-cholan-24-oic acid

HRID 2371860

Reaktionsgleichung

Reaktionsgleichung von HRID 2371860
[O:1]1[CH:6]=[CH:5][CH2:4][CH2:3][CH2:2]1.[CH3:7][C@@H:8]([C@@H:14]1[C@@:18]2([CH3:34])[CH2:19][CH2:20][C@@H:21]3[C@@:26]4([CH3:32])[CH2:27][CH2:28][C@@H:29]([OH:31])[CH2:30][C@H:25]4[CH2:24][C@H:23]([OH:33])[C@H:22]3[C@@H:17]2[CH2:16][CH2:15]1)[CH2:9][CH2:10][C:11]([OH:13])=[O:12].[C:35]1(C)C=[CH:39][C:38](S(O)(=O)=O)=[CH:37][CH:36]=1.[O:46]1CCOCC1>>[O:1]1[CH2:2][CH2:3][CH2:4][CH2:5][CH:6]1[O:31][C@@H:29]1[CH2:28][CH2:27][C@@:26]2([CH3:32])[C@H:25]([CH2:24][C@H:23]([O:33][CH:39]3[CH2:38][CH2:37][CH2:36][CH2:35][O:46]3)[C@@H:22]3[C@@H:21]2[CH2:20][CH2:19][C@@:18]2([CH3:34])[C@H:17]3[CH2:16][CH2:15][C@@H:14]2[C@H:8]([CH3:7])[CH2:9][CH2:10][C:11]([OH:13])=[O:12])[CH2:30]1

Komponenten

5

Edukt 4

HCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 312751,4-DioxaneHCID 31401Ursodeoxycholic Acid

Produkt 1

HCID 228428343alpha,7beta-Ditetrahydropyranyloxy-5beta-cholan-24-oic acid

Versuchsvorschrift

Dihydropyrane (20.28 g; 241 mmoles) was dropped in 16 hrs into an ursodeoxycholic acid solution (30.0 g; 76.72 mmoles) and p-toluenesulphonic acid (1.55 g; 8.15 mmoles) in dioxane (160 ml), kept under magnetic stirring at room temperature. At the end of the addition the reaction mixture was concentrated under vacuum, taken up into ethyl ether (100 ml) then washed with water (3×50 ml) and saturated water (1×50 ml). After drying over sodium sulfate and evaporation of the solvents, the residue (45.00 g) was subjected to flash chromatography on SiO2 (φ=5 cm, h=20 cm): eluting with 95/5 chloroform/methanol, 34.4 g of compound (2) were obtained, (80%); νmax (CHCl3) 1710 cm-1 (C=O); 1H-NMR (CDCl3)δ 0,7 (s, 3H, 18-CH3); 0,9-1,0 (m, 6H, 19-CH3); 3,3-4,05 (m, 6H, 3-CH-, 7-CH-, 2x-OCH2); 4,4-4,7 (m, 2H, 2x-O-CH-O-).

Aufarbeitung

  1. additionAt the end of the addition the reaction mixture
  2. concentrationwas concentrated under vacuum
  3. washthen washed with water (3×50 ml) and saturated water (1×50 ml)
  4. dry with materialAfter drying over sodium sulfate and evaporation of the solvents
  5. washeluting with 95/5 chloroform/methanol

Quellen und Nachweise

ORD-Eintrag
ord-fe209477ecdb4f50965fa0b15518b00b
Quelldatensatz
uspto-grants-1992_03
Patentnummer
US05096898

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