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HRID1356492

反应详情

EQUATION

反应方程式

HRID 1356492 的结构方程式

REACTANTS

反应物

4
结构：O=CO
HCID284

Formic acid

CH2O2

结构：C=O
HCID712

Formaldehyde

CH2O

结构：O
HCID962

Water

H2O

结构：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@H](C)[C@@H](O)[C@]1(C)O
HCID9810601

2-Ethyl-3,4,10-trihydroxy-3,5,8,10,12,14-hexamethyl-15-oxo-11-{[3,4,6-trideoxy-3-(dimethylamino)hexopyranosyl]oxy}-1-oxa-6-azacyclopentadecan-13-yl 2,6-dideoxy-3-C-methyl-3-O-methylhexopyranoside

C37H70N2O12

PRODUCTS

生成物

1
结构：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
HCID447043

Azithromycin

C38H72N2O12

AUXILIARIES

试剂、催化剂与溶剂

1
结构：CC(C)=O
溶剂HCID180

Acetone

C3H6O

CONDITIONS

反应条件

温度
58 °C

PROCEDURE

实验过程

By the methods of the present invention, desmethyl-azithromycin is dissolved in acetone. Formaldehyde and formic acid are added to the solution and the clear solution is heated to reflux (˜58° C.). The mixture is maintained under reflux for about 3 hours then cooled to less than about 40° C. Water is added and the acetone is separated from the reaction mixture by distillation under low vacuum (˜300 mbar). The distillation is stopped when the temperature of the liquid phase reaches ˜40° C./300 mbar. Activated carbon SXI is added and the suspension is mixed for about 1 hour. The activated carbon is then separated from the solution by filtration on a Büchner filter containing Hyflow. The filter cake is washed with water. The pH is adjusted with an NaOH to about 10-10.5 to induce precipitation of azithromycin. The azithromycin suspension is stirred for about 1 hour. The crude azithromycin crude is separated by filtration and washed. Azithromycin is isolated upon drying the filtrate 40° C. in a vacuum oven. Preferably the azithromycin is dried for at least 24 hours. No impurities were detected that were derivatives of azithromycin in the isolated azithromycin Azithromycin dihydrate prepared in accordance with the present invention is suitable formulation and administration for the treatment of susceptible bacterial infections in humans according to the methods and in the amounts set forth in U.S. Pat. No. 4,474,768, cited above.

WORKUP

后处理

  1. temperaturethe clear solution is heated
  2. temperatureThe mixture is maintained
  3. temperatureunder reflux for about 3 hours
  4. temperaturethen cooled to less than about 40° C
  5. customthe acetone is separated from the reaction mixture by distillation under low vacuum (˜300 mbar)
  6. distillationThe distillation
  7. customreaches ˜40° C.
  8. additionActivated carbon SXI is added
  9. additionthe suspension is mixed for about 1 hour
  10. customThe activated carbon is then separated from the solution by filtration on a Büchner
  11. filtrationfilter
  12. additioncontaining Hyflow
  13. washThe filter cake is washed with water
  14. customprecipitation of azithromycin
  15. customThe crude azithromycin crude is separated by filtration
  16. washwashed