Acetic Anhydride → Erythromycin 2'-acetate

HRID 2256385Notes

Reaction equation

HRID 2256385 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-5f533f91ca0f462a9f708b59c8047b5f
Source dataset
uspto-grants-1997_08
Patent number
US05654411

Reaction notes

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