Methyl iodide → HCID 9960651, Verbindung

HRID 2305413Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2305413
[CH:1]1([CH2:4][N:5]2[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@H:10]([N:24]([CH3:34])[C:25](=[O:33])/[CH:26]=[CH:27]/[C:28]3[CH:32]=[CH:31][O:30][CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:35])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:3][CH2:2]1.[C:36](OCC)(=O)C.C[I:43]>CO>[I-:43].[CH:1]1([CH2:4][N+:5]2([CH3:36])[CH2:23][CH2:22][C@:12]34[C:13]5[C:14]6[O:21][C@H:11]3[C@H:10]([N:24]([CH3:34])[C:25](=[O:33])/[CH:26]=[CH:27]/[C:28]3[CH:32]=[CH:31][O:30][CH:29]=3)[CH2:9][CH2:8][C@@:7]4([OH:35])[C@H:6]2[CH2:19][C:18]=5[CH:17]=[CH:16][C:15]=6[OH:20])[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 6445230(E)-N-(17-(Cyclopropylmethyl)-4,5alpha-epoxy-3,14-dihydroxymorphinan-6beta-yl)-3-(furan-3-yl)-N-methylprop-2-enamide

Produkt 1

HCID 9960651HCID 9960651, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

17-cyclopropylmethyl-3,14β-dihydroxy-4,5α-epoxy-6β-(N-methyl-trans-3-(3-furyl)acrylamido)morphinan 2.0699 g (4.3 mmol), ethyl acetate 60 ml, methanol 6 ml, and methyl iodide 1.3 ml were placed together in a container to be sealed, and, while being sealed, was stirred at 100° C. for four days. To the reaction solution was added methanol 60 ml; the precipitated solid was dissolved and concentrated; and to the resulting residue was added distilled water 400 ml. This aqueous solution was washed with chloroform (100 ml×7); the water phase was concentrated; the resulting residue was recrystallized from ethyl acetate-methanol; and the resulting crystal was dissolved in distilled water 500 ml. This aqueous solution was washed with chloroform (100 ml×3); the water phase was concentrated; the resulting residue was recrystallized three times from methanol; and the compound in the title 102 mg was obtained.

Aufarbeitung

  1. customto be sealed
  2. customwhile being sealed
  3. dissolutionthe precipitated solid was dissolved
  4. concentrationconcentrated
  5. additionand to the resulting residue was added
  6. distillationdistilled water 400 ml
  7. washThis aqueous solution was washed with chloroform (100 ml×7)
  8. concentrationthe water phase was concentrated
  9. customthe resulting residue was recrystallized from ethyl acetate-methanol
  10. dissolutionand the resulting crystal was dissolved in distilled water 500 ml
  11. washThis aqueous solution was washed with chloroform (100 ml×3)
  12. concentrationthe water phase was concentrated
  13. customthe resulting residue was recrystallized three times from methanol
  14. customand the compound in the title 102 mg was obtained

Quellen und Nachweise

ORD-Eintrag
ord-caf0f5af38694e0297c26cfc01ef0429
Quelldatensatz
uspto-grants-2002_08
Patentnummer
US06440987B1

Notizen zur Reaktion

Wird geladen…