Potassium Carbonate → Erythromycin - Impurity F

HRID 2111514

Reaktionsgleichung

Reaktionsgleichung von HRID 2111514
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH2:8][C@H:9]1[O:24][C:22](=[O:23])[C@H:21]([CH3:25])[C@@H:20]([O:26][C@@H:27]2[O:32][C@@H:31]([CH3:33])[C@H:30]([OH:34])[C@@:29]([O:36][CH3:37])([CH3:35])[CH2:28]2)[C@H:19]([CH3:38])[C@@H:18]([O:39][C@@H:40]2[O:45][C@H:44]([CH3:46])[CH2:43][C@H:42]([N:47]([CH3:49])[CH3:48])[C@H:41]2[OH:50])[C@:16]2([CH3:51])[O:17][C:13](=[C:14]([CH3:52])[CH2:15]2)[C@H:12]([CH3:53])[C@@H:11]([OH:54])[C@@:10]1([OH:56])[CH3:55]>CO>[CH3:53][CH2:12][C@@H:11]([OH:54])[C@@:10]([OH:56])([C@@H:9]1[O:24][C:22](=[O:23])[C@H:21]([CH3:25])[C@@H:20]([O:26][C@@H:27]2[O:32][C@@H:31]([CH3:33])[C@H:30]([OH:34])[C@@:29]([O:36][CH3:37])([CH3:35])[CH2:28]2)[C@H:19]([CH3:38])[C@@H:18]([O:39][C@@H:40]2[O:45][C@H:44]([CH3:46])[CH2:43][C@H:42]([N:47]([CH3:49])[CH3:48])[C@H:41]2[OH:50])[C@:16]2([CH3:51])[O:17][C:13](=[C:14]([CH3:52])[CH2:15]2)[C@@H:8]1[CH3:7])[CH3:55]

Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 83954Erythromycin A enol ether

Produkt 1

HCID 9875064Erythromycin - Impurity F

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Synthesis of EM701 was disclosed in detail in WO 02/14338 A1. A glacial acetic acid solution of erythromycin was stirred at room temperature for 2 hours, and aqueous sodium hydrogencarbonate solution was slowly added and neutralized. The reaction mixture was extracted with chloroform. The organic layer was dehydrated by adding anhydrous sodium sulfate, which was removed off by filtration to obtain crude product. The crude product was purified by silica gel column chromatography with chloroform-methanol-aqueous ammonia (10:0.5:0.01→10:1:0.05) to obtain erythromycin A enol ether. Potassium carbonate was added to methanol solution of erythromycin A enol ether and refluxed for 2 hours. After solvent was removed, the residue was dissolved in aqueous sodium hydrogencarbonate and the mixture was extracted with chloroform. The extract was dehydrated with sodium sulfate, filtered and distilled off. The obtained crude product was purified by silica gel column chromatography with chloroform-methanol-aqueous ammonia (10:0.5:0.01→10:1:0.05) to obtain EM701 (white powder).

Aufarbeitung

  1. temperaturerefluxed for 2 hours
  2. customAfter solvent was removed
  3. dissolutionthe residue was dissolved in aqueous sodium hydrogencarbonate
  4. extractionthe mixture was extracted with chloroform
  5. filtrationfiltered
  6. distillationdistilled off
  7. customThe obtained crude product
  8. customwas purified by silica gel column chromatography with chloroform-methanol-aqueous ammonia (10:0.5:0.01→10:1:0.05)

Quellen und Nachweise

ORD-Eintrag
ord-db4a751f93bf49fdb5f97d0385d11c79
Quelldatensatz
uspto-grants-2009_04
Patentnummer
US07521428B2

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