Iodine → HCID 102209284, Verbindung

HRID 1582377Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1582377
C([O-])(=O)C.[Na+].II.[CH3:8][CH2:9][C@@H:10]([OH:57])[C@@:11]([OH:56])([C@@H:13]1[O:26][C:24](=[O:25])[C@H:23]([CH3:27])[C@@H:22]([O:28][C@@H:29]2[O:34][C@@H:33]([CH3:35])[C@H:32]([OH:36])[C@@:31]([O:38][CH3:39])([CH3:37])[CH2:30]2)[C@H:21]([CH3:40])[C@@H:20]([O:41][C@@H:42]2[O:47][C@H:46]([CH3:48])[CH2:45][C@H:44]([N:49](C)[CH3:50])[C@H:43]2[OH:52])[C@:18]2([CH3:53])[O:19][C:15](=[C:16]([CH3:54])[CH2:17]2)[C@@H:14]1[CH3:55])[CH3:12].[OH-].[Na+]>N.O.CO>[CH3:8][CH2:9][C@@H:10]([OH:57])[C@@:11]([OH:56])([C@H:13]1[O:26][C:24](=[O:25])[C@H:23]([CH3:27])[C@@H:22]([O:28][C@@H:29]2[O:34][C@@H:33]([CH3:35])[C@H:32]([OH:36])[C@@:31]([O:38][CH3:39])([CH3:37])[CH2:30]2)[C@H:21]([CH3:40])[C@@H:20]([O:41][C@@H:42]2[O:47][C@H:46]([CH3:48])[CH2:45][C@H:44]([NH:49][CH3:50])[C@H:43]2[OH:52])[C@:18]2([CH3:53])[O:19][C:15](=[C:16]([CH3:54])[CH2:17]2)[C@@H:14]1[CH3:55])[CH3:12]

Komponenten

8

Edukt 4

HCID 807IodineHCID 14798Sodium HydroxideHCID 517045Sodium AcetateHCID 9875064LY 267108

Produkt 1

HCID 102209284HCID 102209284, VerbindungAusbeute 70,5 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 222AmmoniaLösungsmittelHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel2×

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

Sodium acetate (3.9 g, 48.5 mmol) and iodine (2.5 g, 9.7 mmol) were added in this order to methanol (52.0 mL)-water (13.0 mL) solution of EM701 (6.9 g, 9.7 mmol) at room temperature, and stirred at 50° C. for 3 hours. During the stirring, 1N aqueous solution of sodium hydroxide was added to maintain at pH 8-9 continuously. After confirming the completion of the reaction by TLC, the reaction mixture was diluted with aqueous ammonia (7.5 mL)-water (200 mL), and extracted with dichloromethane. After dehydrating the organic layer with sodium sulfate, the sodium sulfate was removed by filtration and distilled off the solvent to obtain crude substance. The crude substance was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05) to obtain EM703 (4.8 g, Yield: 70%, white powder). EM703: m. p.: 177-180° C.

Aufarbeitung

  1. temperatureto maintain at pH 8-9 continuously
  2. customthe completion of the reaction by TLC
  3. extractionextracted with dichloromethane
  4. customthe sodium sulfate was removed by filtration
  5. distillationdistilled off the solvent
  6. customto obtain crude substance
  7. customThe crude substance was purified by silica gel column chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05)

Quellen und Nachweise

ORD-Eintrag
ord-9132f33ffd7e4f80983e99ab4dc00728
Quelldatensatz
uspto-grants-2004_05
Patentnummer
US06734292B1

Notizen zur Reaktion

Wird geladen…