Potassium Carbonate → Erythromycin - Impurity F

HRID 1582376

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HRID 1582376 반응식
C(=O)([O-])[O-].[K+].[K+].[CH3:7][CH2:8][C@H:9]1[O:24][C:22](=[O:23])[C@H:21]([CH3:25])[C@@H:20]([O:26][C@@H:27]2[O:32][C@@H:31]([CH3:33])[C@H:30]([OH:34])[C@@:29]([O:36][CH3:37])([CH3:35])[CH2:28]2)[C@H:19]([CH3:38])[C@@H:18]([O:39][C@@H:40]2[O:45][C@H:44]([CH3:46])[CH2:43][C@H:42]([N:47]([CH3:49])[CH3:48])[C@H:41]2[OH:50])[C@:16]2([CH3:51])[O:17][C:13](=[C:14]([CH3:52])[CH2:15]2)[C@H:12]([CH3:53])[C@@H:11]([OH:54])[C@@:10]1([OH:56])[CH3:55]>>[CH3:53][CH2:12][C@@H:11]([OH:54])[C@@:10]([OH:56])([C@@H:9]1[O:24][C:22](=[O:23])[C@H:21]([CH3:25])[C@@H:20]([O:26][C@@H:27]2[O:32][C@@H:31]([CH3:33])[C@H:30]([OH:34])[C@@:29]([O:36][CH3:37])([CH3:35])[CH2:28]2)[C@H:19]([CH3:38])[C@@H:18]([O:39][C@@H:40]2[O:45][C@H:44]([CH3:46])[CH2:43][C@H:42]([N:47]([CH3:49])[CH3:48])[C@H:41]2[OH:50])[C@:16]2([CH3:51])[O:17][C:13](=[C:14]([CH3:52])[CH2:15]2)[C@@H:8]1[CH3:7])[CH3:55]

참가 물질

3

반응물 2

HCID 11430Potassium CarbonateHCID 83954Erythromycin A enol ether

생성물 1

HCID 9875064Erythromycin - Impurity F수율 78%

실험 절차

Glacial acetic acid solution of erythromycin A (12.4 g, 16.9 mmol) was stirred at room temperature for 2 hours, added slowly aqueous sodium hydrogen carbonate and neutralized. The reaction mixture was extracted with chloroform, dehydrated the organic layer with sodium sulfate, filtered off the sodium sulfate and removed the solvent by distillation to obtain crude substance. The crude substance was purified with silica gel chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05) to obtain EM201 (7.7 g, 63%). Subsequently, potassium carbonate (1.4 g, 10.6 mmol) was added to the methanol solution (100 ml) of EM 201 (7.6 g, 10.6 mmol) and refluxed for 2 hours. After distilled off the solvent, the residue was dissolved in aqueous sodium hydrogen carbonate and extracted with chloroform. The mixture was dehydrated with sodium sulfate, filtered and removed the sodium sulfate, then the obtained crude substance was purified by silica gel chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05) to obtain EM701 (5.9 g, 78%, white powder).

후처리

  1. temperaturerefluxed for 2 hours
  2. distillationAfter distilled off the solvent
  3. dissolutionthe residue was dissolved in aqueous sodium hydrogen carbonate
  4. extractionextracted with chloroform
  5. filtrationfiltered
  6. customremoved the sodium sulfate
  7. customthe obtained crude substance
  8. customwas purified by silica gel chromatography (chloroform:methanol:aqueous ammonia=10:0.5:0.01→10:1:0.05)

출처 및 근거

ORD 기록
ord-caa3fbacc7b24026b2046a3e8052905e
출처 데이터셋
uspto-grants-2004_05
특허 번호
US06734292B1

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