Methyl iodide → HCID 9960651, compound

HRID 2305413Notes

Reaction equation

HRID 2305413 reaction equation
[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

Participants

5

Reactant 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

Product 1

HCID 9960651HCID 9960651, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
100 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-caf0f5af38694e0297c26cfc01ef0429
Source dataset
uspto-grants-2002_08
Patent number
US06440987B1

Reaction notes

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