Clarithromycin formate → Clarithromycin

HRID 1278900Notes

Reaction equation

HRID 1278900 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-])=O>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]([CH3:42])[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]

Participants

3

Reactant 1

HCID 86758498Clarithromycin formate

Product 1

HCID 84029Clarithromycin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Specifically, clarithromycin formate is dissolved in a mixture of water and a water-miscible organic solvent at a temperature in the range of room temperature to the boiling point of the solvent for a period sufficient to make a solution. Then, the solution is filtered and a base is added to the filtrate to neutralize and make pH of the solution 7 to 12. The solution may then be optionally kept at a temperature ranging from room temperature to the boiling point of the solvent for 10 minutes to 1 hour. The resulting solution is cooled to a temperature in the range of −20° C. to room temperature with or without stirring for a period sufficient to precipitate Form II crystals of clarithromycin. Finally, the precipitated crystals are filtered and dried in a conventional manner to give Form II crystals of clarithromycin.

Workup

  1. filtrationThen, the solution is filtered
  2. additiona base is added to the filtrate
  3. waitranging from room temperature to the boiling point of the solvent for 10 minutes to 1 hour
  4. temperatureThe resulting solution is cooled to a temperature in the range of −20° C. to room temperature with or
  5. customto precipitate Form II crystals of clarithromycin
  6. filtrationFinally, the precipitated crystals are filtered
  7. customdried in a conventional manner

Sources & evidence

ORD record
ord-fc4c48704a0747ab9d283024da2a60bb
Source dataset
uspto-grants-2002_09
Patent number
US06444796B1

Reaction notes

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