Allyl bromide → Rocuronium Bromide

HRID 1988569

Reaktionsgleichung

Reaktionsgleichung von HRID 1988569
C(=O)([O-])[O-].[Na+].[Na+].[CH2:7]([Br:10])[CH:8]=[CH2:9].[C:11]([O:14][C@H:15]1[C@@H:20]([N:21]2[CH2:25][CH2:24][CH2:23][CH2:22]2)[CH2:19][C@H:18]2[C@H:26]3[C@H:36]([CH2:37][CH2:38][C@:16]12[CH3:17])[C@:34]1([CH3:35])[C@H:29]([CH2:30][C@H:31]([OH:45])[C@@H:32]([N:39]2[CH2:44][CH2:43][O:42][CH2:41][CH2:40]2)[CH2:33]1)[CH2:28][CH2:27]3)(=[O:13])[CH3:12]>ClCCl>[Br-:10].[C:11]([O:14][C@H:15]1[C@@H:20]([N+:21]2([CH2:9][CH:8]=[CH2:7])[CH2:22][CH2:23][CH2:24][CH2:25]2)[CH2:19][C@H:18]2[C@H:26]3[C@H:36]([CH2:37][CH2:38][C@:16]12[CH3:17])[C@:34]1([CH3:35])[C@H:29]([CH2:30][C@H:31]([OH:45])[C@@H:32]([N:39]2[CH2:40][CH2:41][O:42][CH2:43][CH2:44]2)[CH2:33]1)[CH2:28][CH2:27]3)(=[O:13])[CH3:12]

Komponenten

5

Edukt 3

HCID 7841Allyl bromideHCID 10340Sodium CarbonateHCID 16064933(2b,3a,5a,16b,17b)-17-Acetoxy-3-hydroxy-2-(4-morpholinyl)-16-(1-pyrrolidinyl)androstane2×

Produkt 1

HCID 441351Rocuronium Bromide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
22.5 °C

Versuchsvorschrift

In a three neck flask equipped with heated mantle, thermometer and magnetic stirrer, was charged dichloromethane (20 mL), sodium carbonate (2.0 g, 0.081 mol) and slowly allyl bromide (0.692 mL, 0.00818 mol) at 20-22° C. under N2 atmosphere. The mixture was stirred during 5 min and 2β-(4-morpholinyl)-16β-(1-pyrrolidinyl)-5α-androstan-3α,17β-diol 17-acetate (Compound VIII) (2.0 g, 4.09×10−3 mol) was added. The resulting mixture was stirred during 5-10 min. The resulting solution was stirred under reflux for 22 hours. The mixture was then cooled to room temperature (20-25° C.) and filtered (membrane 0.45 microns) under nitrogen atmosphere. The solvent was removed under vacuum keeping the temperature below 20° C. The foam obtained was dissolved with dichloromethane (10 mL) and concentrated under vacuum keeping the temperature below 20° C.; this procedure was repeated twice. Once again the residue was dissolved at room temperature under nitrogen atmosphere in dichloromethane (22 mL).

Aufarbeitung

  1. customIn a three neck flask equipped
  2. temperaturewith heated mantle
  3. stirringThe resulting mixture was stirred during 5-10 min
  4. stirringThe resulting solution was stirred
  5. temperatureunder reflux for 22 hours
  6. filtrationfiltered (membrane 0.45 microns) under nitrogen atmosphere
  7. customThe solvent was removed under vacuum
  8. customthe temperature below 20° C
  9. customThe foam obtained
  10. concentrationconcentrated under vacuum
  11. customthe temperature below 20° C.
  12. dissolutionOnce again the residue was dissolved at room temperature under nitrogen atmosphere in dichloromethane (22 mL)

Quellen und Nachweise

ORD-Eintrag
ord-7628d06328d143c08361ef07923c3693
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07642246B2

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