Acetic Anhydride → Erythromycin 2'-acetate

HRID 355665

反応式

HRID 355665 の反応式
[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]

参加物

4

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-e24f9892a9344ca9bf340c33e656ffc1
出典データセット
uspto-grants-1998_11
特許番号
US05834438

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