Reaction #927272

ord-ea935c98fbb2494482fe718f39719003

Reaction equation

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
azithromycin
CCO
ethanol
→
CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O.CC[O-]
azithromycin ethanolate

Reactants

CC[C@H]1OC(=O)[C@H](C)[C@@H](O[C@H]2C[C@@](C)(OC)[C@@H](O)[C@H](C)O2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@](C)(O)C[C@@H](C)CN(C)[C@H](C)[C@@H](O)[C@]1(C)O
azithromycin
CCO
ethanol

Reagents

None

Solvents

O
water
O
water
O
water

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    Otherequipped with a mechanical stirrer, a condenser
  2. 2
    Temperaturethe solution was heated at a constant temperature gradient so as
  3. 3
    OtherWhen 55° C.
  4. 4
    workup.ADDITIONwas added
  5. 5
    TemperatureThe suspension was then cooled from 55° C. to 20° C. over 2 hours
  6. 6
    FiltrationThe precipitate was filtered
  7. 7
    OtherAfter drying

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.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US06365574B2uspto-grants-2002_04