Acetic Anhydride → Erythromycin 2'-acetate

HRID 1901430Notes

Reaction equation

HRID 1901430 reaction equation
[C:1](OC(=O)C)(=[O:3])[CH3:2].[CH3:8][CH2:9][C@H:10]1[O:25][C:23](=[O:24])[C@H:22]([CH3:26])[C@@H:21]([O:27][C@@H:28]2[O:33][C@@H:32]([CH3:34])[C@H:31]([OH:35])[C@@:30]([O:37][CH3:38])([CH3:36])[CH2:29]2)[C@H:20]([CH3:39])[C@@H:19]([O:40][C@@H:41]2[O:46][C@H:45]([CH3:47])[CH2:44][C@H:43]([N:48]([CH3:50])[CH3:49])[C@H:42]2[OH:51])[C@@:18]([OH:53])([CH3:52])[CH2:17][C@@H:16]([CH3:54])[C:14](=[O:15])[C@H:13]([CH3:55])[C@@H:12]([OH:56])[C@@:11]1([OH:58])[CH3:57]>C(Cl)Cl>[CH3:8][CH2:9][C@H:10]1[O:25][C:23](=[O:24])[C@H:22]([CH3:26])[C@@H:21]([O:27][C@@H:28]2[O:33][C@@H:32]([CH3:34])[C@H:31]([OH:35])[C@@:30]([O:37][CH3:38])([CH3:36])[CH2:29]2)[C@H:20]([CH3:39])[C@@H:19]([O:40][C@@H:41]2[O:46][C@H:45]([CH3:47])[CH2:44][C@H:43]([N:48]([CH3:49])[CH3:50])[C@H:42]2[O:51][C:1]([CH3:2])=[O:3])[C@@:18]([OH:53])([CH3:52])[CH2:17][C@@H:16]([CH3:54])[C:14](=[O:15])[C@H:13]([CH3:55])[C@@H:12]([OH:56])[C@@:11]1([OH:58])[CH3:57]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 12560Erythromycin

Product 1

HCID 114919Erythromycin 2'-acetateYield 71%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Acetic anhydride (3.5 ml, 1.2 eq.) was added at ambient temperature to a solution of erythromycin A (23 g, commercially available from Abbott Laboratories) dissolved in 350 mL of methylene chloride. The reaction mixture was stirred for 12 hours at room temperature. The methylene chloride solution was washed twice with 100 mL of 1% sodium bicarbonate solution, once with 100 mL of water, dried over anhydrous sodium sulfate and filtered. Solvent was removed in vacuo to afford a white solid which was recrystallized from acetonitrile to the product in 71% yield.

Workup

  1. washThe methylene chloride solution was washed twice with 100 mL of 1% sodium bicarbonate solution, once with 100 mL of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. customSolvent was removed in vacuo
  5. customto afford a white solid which
  6. customwas recrystallized from acetonitrile to the product in 71% yield

Sources & evidence

ORD record
ord-e1f525229fe5481091ae5f6788f7b585
Source dataset
uspto-grants-1996_11
Patent number
US05578579

Reaction notes

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