Methanol → Clarithromycin

HRID 1065940

Reaktionsgleichung

Reaktionsgleichung von HRID 1065940
P([O-])([O-])([O-])=O.[CH3:6][CH2:7][C@H:8]1[O:23][C:21](=[O:22])[C@H:20]([CH3:24])[C@@H:19]([O:25][C@@H:26]2[O:31][C@@H:30]([CH3:32])[C@H:29]([OH:33])[C@@:28]([O:35][CH3:36])([CH3:34])[CH2:27]2)[C@H:18]([CH3:37])[C@@H:17]([O:38][C@@H:39]2[O:44][C@H:43]([CH3:45])[CH2:42][C@H:41]([N:46]([CH3:48])[CH3:47])[C@H:40]2[OH:49])[C@@:16]([OH:51])([CH3:50])[CH2:15][C@@H:14]([CH3:52])[C:12](=[O:13])[C@H:11]([CH3:53])[C@@H:10]([OH:54])[C@@:9]1([OH:56])[CH3:55].[CH3:57]O>>[CH3:6][CH2:7][C@H:8]1[O:23][C:21](=[O:22])[C@H:20]([CH3:24])[C@@H:19]([O:25][C@@H:26]2[O:31][C@@H:30]([CH3:32])[C@H:29]([OH:33])[C@@:28]([O:35][CH3:36])([CH3:34])[CH2:27]2)[C@H:18]([CH3:37])[C@@H:17]([O:38][C@@H:39]2[O:44][C@H:43]([CH3:45])[CH2:42][C@H:41]([N:46]([CH3:47])[CH3:48])[C@H:40]2[OH:49])[C@@:16]([O:51][CH3:57])([CH3:50])[CH2:15][C@@H:14]([CH3:52])[C:12](=[O:13])[C@H:11]([CH3:53])[C@@H:10]([OH:54])[C@@:9]1([OH:56])[CH3:55]

Komponenten

4

Edukt 3

HCID 887Methanol2×HCID 1061PhosphateHCID 12560Erythromycin

Produkt 1

HCID 84029Clarithromycin

Versuchsvorschrift

Each fraction was analyzed by thin layer chromatography (E. Merck Darmstadt. thin layer chromatography plate silica gel 60 silanized precoated, thickness 0.25 mm), developing in a mixture of methanol and a 0.1 M phosphate buffer solution (pH 7.0) (3:2). The fractions having Rf value 0.42 (c.f., erythromycin A, Rf value 0.46) were combined and most of the methanol was evaporated in vacuo. The residue was made alkaline with sodium carbonate and extracted with chloroform. The chloroform layer was washed with water, dried and concentrated in vacuo. The crystals obtained were recrystallized from a mixture of chloroform and diisopropyl ether (1:2), giving 700 mg of pure 6-O-methylerythromycin A (formula(I), R1 is hydrogen) in the form of colorless needles.

Aufarbeitung

  1. customwas evaporated in vacuo
  2. extractionextracted with chloroform
  3. washThe chloroform layer was washed with water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe crystals obtained
  7. customwere recrystallized from a mixture of chloroform and diisopropyl ether (1:2)

Quellen und Nachweise

ORD-Eintrag
ord-6817c63addcc4779b9f827a3ce50c03c
Quelldatensatz
uspto-grants-1982_05
Patentnummer
US04331803

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