Acetyl chloride → Methyl cholate

HRID 375704

Reaktionsgleichung

Reaktionsgleichung von HRID 375704
[C:1](OC)(=O)CC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(CCCC2)CC3)CC1)C.C(Cl)(=O)C.[CH3:32][C@@H:33]([C@@H:39]1[C@@:43]2([CH3:60])[C@@H:44]([OH:59])[CH2:45][C@@H:46]3[C@@:51]4([CH3:57])[CH2:52][CH2:53][C@@H:54]([OH:56])[CH2:55][C@H:50]4[CH2:49][C@@H:48]([OH:58])[C@H:47]3[C@@H:42]2[CH2:41][CH2:40]1)[CH2:34][CH2:35][C:36]([OH:38])=[O:37]>CO>[CH3:32][C@@H:33]([C@@H:39]1[C@@:43]2([CH3:60])[C@@H:44]([OH:59])[CH2:45][C@@H:46]3[C@@:51]4([CH3:57])[CH2:52][CH2:53][C@@H:54]([OH:56])[CH2:55][C@H:50]4[CH2:49][C@@H:48]([OH:58])[C@H:47]3[C@@H:42]2[CH2:41][CH2:40]1)[CH2:34][CH2:35][C:36]([O:38][CH3:1])=[O:37]

Komponenten

5

Edukt 3

HCID 6367Acetyl chlorideHCID 221493Cholic AcidHCID 54509003Methyl cholanate

Produkt 1

HCID 10960835Methyl cholateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
10 °C

Versuchsvorschrift

Preparation of the starting compounds of the formula III using the example of methyl cholanate (Fieset et al., J. Am. Chem. Soc. 74, 1952, 3309) ##STR6## 450 ml of acetyl chloride are slowly added dropwise to 4.5 l of methanol, while cooling with ice, such that the temperature does not exceed 10° to 15° C. After the addition, the mixture is subsequently stirred at about 10° C. for a further 15 minutes. 600 g (1.47 mol) of cholic acid are then introduced at about 5° C. The ice-bath is removed, and after a further hour, while stirring, the reaction is ended. The reaction mixture is slowly added to 12 l of water. The mixture is stirred for a further 2 hours and then filtered with suction, and the residue is rinsed with 3 l of water. The crystalline substance is dried in vacuo at 50° C. 610 g (98%) of methyl cholate (melting point 154° C.) are obtained.

Aufarbeitung

  1. temperaturewhile cooling with ice, such that the temperature
  2. customdoes not exceed 10° to 15° C
  3. additionAfter the addition
  4. customThe ice-bath is removed
  5. waitafter a further hour
  6. stirringwhile stirring
  7. additionThe reaction mixture is slowly added to 12 l of water
  8. stirringThe mixture is stirred for a further 2 hours
  9. filtrationfiltered with suction
  10. washthe residue is rinsed with 3 l of water
  11. customThe crystalline substance is dried in vacuo at 50° C

Quellen und Nachweise

ORD-Eintrag
ord-965ece26e512462fb8524b1b5d567c78
Quelldatensatz
uspto-grants-1996_01
Patentnummer
US05486626

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