Hydrochloric Acid → Clarithromycin

HRID 1358912Notes

Reaction equation

HRID 1358912 reaction equation
Cl.[CH3:2][CH2:3][C@H:4]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]([CH3:49])[C:8](=[O:9])[C@H:7]([CH3:50])[C@@H:6]([OH:51])[C@@:5]1([OH:53])[CH3:52].Cl>O>[CH3:2][CH2:3][C@H:4]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]([CH3:49])[C:8](=[O:9])[C@H:7]([CH3:50])[C@@H:6]([OH:51])[C@@:5]1([OH:53])[CH3:52]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 70018967HCID 70018967, compound

Product 1

HCID 84029Clarithromycin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g of crude clarithromycin, as obtained in a production process, e.g. as conventional, are suspended in 300 ml of water at 25 to 30° C. 7 ml of 1N hydrochloric acid is added to adjust the pH to about 2.5 to 3.0 resulting in a slightly turbid solution of clarithromycin hydrochloride. The solution is filtered, and to the resulting clear solution an aqueous sodium hydroxide solution is added to adjust the pH to about 8.5. Clarithromycin in the form of a free base precipitates and the resulting suspension is filtered. Pure crystalline clarithromycin in the form of a stable hydrate is obtained and dried at 65° C.

Workup

  1. filtrationThe solution is filtered
  2. additionto the resulting clear solution an aqueous sodium hydroxide solution is added
  3. customClarithromycin in the form of a free base precipitates
  4. filtrationthe resulting suspension is filtered

Sources & evidence

ORD record
ord-bd448eb2ed9b44ce8bb5cf8b30566b11
Source dataset
uspto-grants-2003_07
Patent number
US06599886B2

Reaction notes

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