Acetic Anhydride → Erythromycin 2'-acetate

HRID 355665

반응식

HRID 355665 반응식
[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]

참가 물질

4

반응물 2

HCID 7918Acetic AnhydrideHCID 12560Erythromycin

생성물 1

HCID 114919Erythromycin 2'-acetate수율 71%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e24f9892a9344ca9bf340c33e656ffc1
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05834438

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