Clarithromycin → Clarithromycin

HRID 1586374Notes

Reaction equation

HRID 1586374 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]([O:46][CH3:47])([CH3:45])[CH2:10][C@@H:9]([CH3:48])[C:7](=[O:8])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51]>C(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]([O:46][CH3:47])([CH3:45])[CH2:10][C@@H:9]([CH3:48])[C:7](=[O:8])[C@H:6]([CH3:49])[C@@H:5]([OH:50])[C@@:4]1([OH:52])[CH3:51].[CH2:7]([O-:8])[CH3:6]

Participants

4

Reactant 1

HCID 84029Clarithromycin

Product 2

HCID 84029ClarithromycinHCID 1194401-Hydroxyethyl radical

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 6-O-methylerythromycin A (20 g), prepared as described above, and ethanol (200 mL) was warmed to reflux and the insoluble material (11.2 g) was removed by filtration. The filtrate was transferred to a clean flask and heated to reflux. The clear solution was allowed to cool to ambient temperature and then was further cooled in an ice bath. The liquid was decanted to leave 6-O-methylerythromycin A form 0 ethanolate which was sealed in a container without further drying. The 2-theta angle positions in the single crystal x-ray diffraction pattern of 6-O-methylerythromycin A form 0-ethanolate are 4.72°±0.2, 6.60°±0.2, 7.72°±0.2, 9.30°±0.2, 10.40°±0.2, 11.10°±0.2, 11.86°±0.2, 12.72°±0.2, 13.90°±0.2, 15.02°±0.2, 17.18°±0.2, 18.50°±0.2, 19.08°±0.2, 19.68°±0.2, 23.14°±0.2 and 23.98°±0.2.

Workup

  1. customprepared
  2. temperaturewas warmed
  3. temperatureto reflux
  4. customthe insoluble material (11.2 g) was removed by filtration
  5. customThe filtrate was transferred to a clean flask
  6. temperatureheated to reflux
  7. temperaturewas further cooled in an ice bath
  8. customThe liquid was decanted

Sources & evidence

ORD record
ord-a59b96931cb74ed1ae7b4e2fc17e32c7
Source dataset
uspto-grants-1999_08
Patent number
US05945405

Reaction notes

Loading…