Erythromycin → Erythromycin A enol ether

HRID 1796901

Reaktionsgleichung

Reaktionsgleichung von HRID 1796901
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11](O)([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@:11]2([CH3:45])[O:8][C:7](=[C:9]([CH3:47])[CH2:10]2)[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

Komponenten

4

Edukt 2

HCID 12560ErythromycinHCID 516892Sodium Bicarbonate

Produkt 1

HCID 83954Erythromycin A enol etherAusbeute 63,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

Glacial acetic acid solution of erythromycin (12.4 g) was stirred at room temperature for 2 hours, added slowly aqueous sodium hydrogen carbonate and neutralized. The reaction mixture was extracted with chloroform, dehydrated the organic layer with mirabilite, filtered off the mirabilite and removed the solvent by distillation to obtain crude substance. The crude substance was purified with silica gel column chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05) to obtain EM201 (7.7 g). Subsequently, potassium carbonate (1.4 g) was added to the methanol solution of EM201 (7.6 g) and refluxed for 2 hours. After distilled off the solvent, the residue was dissolved in aqueous sodium hydrogen carbonate and extracted with chloroform. The mixture was dehydrated with mirabilite, filtered and removed the mirabilite, then the obtained crude substance was purified by silicagel column chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05) to obtain EM701 (5.9 g, white powder).

Aufarbeitung

  1. extractionThe reaction mixture was extracted with chloroform
  2. filtrationfiltered off the mirabilite
  3. customremoved the solvent
  4. distillationby distillation
  5. customto obtain crude substance
  6. customThe crude substance was purified with silica gel column chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05)

Quellen und Nachweise

ORD-Eintrag
ord-6cd959970c2049ae810a72e159235497
Quelldatensatz
uspto-grants-2006_04
Patentnummer
US07034005B2

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