Ethanol → Clarithromycin

HRID 652270

Reaktionsgleichung

Reaktionsgleichung von HRID 652270
[CH3:1][CH2:2][C@H:3]1[O:19][C:17](=[O:18])[C@H:16]([CH3:20])[C@@H:15]([O:21][C@@H:22]2[O:27][C@@H:26]([CH3:28])[C@H:25]([OH:29])[C@@:24]([O:31][CH3:32])([CH3:30])[CH2:23]2)[C@H:14]([CH3:33])[C@@H:13]([O:34][C@@H:35]2[O:40][C@H:39]([CH3:41])[CH2:38][C@H:37]([N:42]([CH3:44])[CH3:43])[C@H:36]2[OH:45])[C@@:12]([O:47][CH3:48])([CH3:46])[CH2:11][C@@H:10](C)/[C:7](=N\O)/[C@H](C)[C@@H:5]([OH:51])[C@@:4]1([OH:53])[CH3:52].S([O-])(O)=O.[Na+].[C:59](=O)([O-])[O-].[Na+].[Na+].[CH2:65]([OH:67])[CH3:66]>O>[CH3:1][CH2:2][C@H:3]1[O:19][C:17](=[O:18])[C@H:16]([CH3:20])[C@@H:15]([O:21][C@@H:22]2[O:27][C@@H:26]([CH3:28])[C@H:25]([OH:29])[C@@:24]([O:31][CH3:32])([CH3:30])[CH2:23]2)[C@H:14]([CH3:33])[C@@H:13]([O:34][C@@H:35]2[O:40][C@H:39]([CH3:41])[CH2:38][C@H:37]([N:42]([CH3:43])[CH3:44])[C@H:36]2[OH:45])[C@@:12]([O:47][CH3:48])([CH3:46])[CH2:11][C@@H:10]([CH3:7])[C:65](=[O:67])[C@H:66]([CH3:59])[C@@H:5]([OH:51])[C@@:4]1([OH:53])[CH3:52]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 9962216Clarithromycin 9-OximeHCID 23665763Sodium Bisulfite

Produkt 1

HCID 84029Clarithromycin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel2×

Versuchsvorschrift

3 g of 6-0-methylerythromycin A 9-oxime and 3.27 g of sodium hydrogen sulfite were dissolved in a mixture of 30 ml of ethanol and 30 ml of water, and the solution was refluxed with stirring for 6 hours. The solution was cooled to room temperature, 60 ml of water was added, and the pH of the solution was adjusted to more than 10 with a saturated aqueous sodium carbonate solution. The precipitate which formed was collected by filtration, washed throughly with water and recrystallized from ethanol to give 2.01 g of 6-0-methylerythromycin A. m.p. 223°-225° C.

Aufarbeitung

  1. temperaturethe solution was refluxed
  2. customThe precipitate which formed
  3. filtrationwas collected by filtration
  4. washwashed throughly with water
  5. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-b4a12990adc545aea23213eda824deda
Quelldatensatz
uspto-grants-1987_06
Patentnummer
US04670549

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