Ethanol → Azithromycin ethanolate

HRID 840090

Reaction equation

HRID 840090 reaction equation
[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]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[CH2:8][N:7]([CH3:48])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51].[CH2:53]([OH:55])[CH3:54]>O>[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]([OH:46])([CH3:45])[CH2:10][C@@H:9]([CH3:47])[CH2:8][N:7]([CH3:48])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51].[CH2:53]([O-:55])[CH3:54]

Participants

4

Reactant 2

HCID 702EthanolHCID 447043Azithromycin

Product 1

HCID 86584202Azithromycin ethanolate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Procedure

Ten g of azithromycin crude was introduced into a 0.25 liter three-necked flat flanged jacketed vessel equipped with a mechanical stirrer, a condenser and thermometer and containing 30 ml of absolute ethanol at 20° C. Three ml of water at 20° C. were added and the solution was heated at a constant temperature gradient so as to reach 55° C. after 4 hours. Between 35° C. and 55° C., additional water having a total volume of 11 ml was slowly added at regular time intervals. When 55° C. was reached, the resulting suspension was maintained at this temperature for 2 hours, during which an additional 49 mL of water was added. The suspension was then cooled from 55° C. to 20° C. over 2 hours. The precipitate was filtered. After drying, 9 g of azithromycin ethanolate were obtained.

Workup

  1. customequipped with a mechanical stirrer, a condenser
  2. temperaturethe solution was heated at a constant temperature gradient so as
  3. customWhen 55° C.
  4. additionwas added
  5. temperatureThe suspension was then cooled from 55° C. to 20° C. over 2 hours
  6. filtrationThe precipitate was filtered
  7. customAfter drying

Sources & evidence

ORD record
ord-ea935c98fbb2494482fe718f39719003
Source dataset
uspto-grants-2002_04
Patent number
US06365574B2

Linked notes

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