Methyl iodide → RA Vii

HRID 4467

Reaktionsgleichung

Reaktionsgleichung von HRID 4467
[CH3:1]OC.[CH3:4][C@@H:5]1[NH:40][C:38](=[O:39])[C@@H:37]2[N:41]([CH3:44])[C:42](=[O:43])[C@@H:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[C:34]([CH2:36]2)[CH:33]=[CH:32][C:31]=4[OH:45])=[CH:25][CH:24]=3)[N:20]([CH3:46])[C:18](=[O:19])[C@@H:17]([CH3:47])[NH:16][C:14](=[O:15])[C@H:13]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:12]([CH3:57])[C:10](=[O:11])[C@H:9]([CH3:58])[NH:8][C:6]1=[O:7].C[C@@H]1NC(=O)[C@@H]2N(C)C(=O)[C@@H](CC3C=CC(OC4C=C(C2)C=CC=4O)=CC=3)N(C)C(=O)[C@@H](C)NC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H](C)NC1=O.C[C@@H]1NC(=O)[C@@H]2N(C)C(=O)[C@@H](CC3C=CC(OC4C=C(C2)C=CC=4O)=CC=3)N(C)C(=O)[C@@H](C)NC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H](C)NC1=O.C[C@@H]1NC(=O)[C@@H]2N(C)C(=O)[C@@H](CC3C=CC(OC4C=C(C2)C=CC=4O)=CC=3)N(C)C(=O)[C@@H](C)NC(=O)[C@H](CC2C=CC(OC)=CC=2)N(C)C(=O)[C@H](C)NC1=O.O.O.O.O.O.CI>COCCOC>[CH3:4][C@H:5]1[NH:40][C:38](=[O:39])[C@H:37]2[N:41]([CH3:44])[C:42](=[O:43])[C@H:21]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][C:30]4[CH:35]=[C:34]([CH2:36]2)[CH:33]=[CH:32][C:31]=4[O:45][CH3:1])=[CH:25][CH:24]=3)[N:20]([CH3:46])[C:18](=[O:19])[C@H:17]([CH3:47])[NH:16][C:14](=[O:15])[C@H:13]([CH2:48][C:49]2[CH:54]=[CH:53][C:52]([O:55][CH3:56])=[CH:51][CH:50]=2)[N:12]([CH3:57])[C:10](=[O:11])[C@H:9]([CH3:58])[NH:8][C:6]1=[O:7]

Komponenten

5

Edukt 3

HCID 6328Methyl iodideHCID 8254Dimethyl EtherHCID 11979419Bouvardin, 5-(N-methyl-L-tyrosine)-

Produkt 1

HCID 3034401RA Vii

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel

Versuchsvorschrift

In 10 ml of anhydrous 1,2-dimethoxy ethane, 100 mg of the methylether derivative of TPC-A was dissolved and 240 mg of potassium fluoride-alumina and excess amount of methyl iodide were added and the mixture was shielded from the light while stirring at room temperature overnight. After completion of the reaction, the solution was filtered, the filtrate was subjected to distillation in vacuo to remove solvent and the residue obtained was purified by P-TLC followed by the recrystallization from methanol to obtain N-methyl derivative of the methylether of TPC-A (98 mg) as colorless crystal having m.p. of 285° to 292° C. (decomp) and [α]D27 of -166° (CHCl3).

Aufarbeitung

  1. customAfter completion of the reaction
  2. filtrationthe solution was filtered
  3. distillationthe filtrate was subjected to distillation in vacuo
  4. customto remove solvent
  5. customthe residue obtained
  6. customwas purified by P-TLC
  7. customfollowed by the recrystallization from methanol

Quellen und Nachweise

ORD-Eintrag
ord-646e134c4c8349d79582f85770153680
Quelldatensatz
uspto-grants-1988_02
Patentnummer
US04725578

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