Erythromycin → Erythromycin A enol ether

HRID 2111513

반응식

HRID 2111513 반응식
CC[C@@H](O)[C@@](O)([C@@H]1OC(=O)[C@H](C)[C@@H](O[C@@H]2O[C@@H](C)[C@H](O)[C@@](OC)(C)C2)[C@H](C)[C@@H](O[C@@H]2O[C@H](C)C[C@H](N(C)C)[C@H]2O)[C@]2(C)OC(=C(C)C2)[C@@H]1C)C.[CH3:51][CH2:52][C@H:53]1[O:68][C:66](=[O:67])[C@H:65]([CH3:69])[C@@H:64]([O:70][C@@H:71]2[O:76][C@@H:75]([CH3:77])[C@H:74]([OH:78])[C@@:73]([O:80][CH3:81])([CH3:79])[CH2:72]2)[C@H:63]([CH3:82])[C@@H:62]([O:83][C@@H:84]2[O:89][C@H:88]([CH3:90])[CH2:87][C@H:86]([N:91]([CH3:93])[CH3:92])[C@H:85]2[OH:94])[C@@:61](O)([CH3:95])[CH2:60][C@@H:59]([CH3:97])[C:57](=[O:58])[C@H:56]([CH3:98])[C@@H:55]([OH:99])[C@@:54]1([OH:101])[CH3:100].C(=O)([O-])O.[Na+]>C(O)(=O)C>[CH3:51][CH2:52][C@H:53]1[O:68][C:66](=[O:67])[C@H:65]([CH3:69])[C@@H:64]([O:70][C@@H:71]2[O:76][C@@H:75]([CH3:77])[C@H:74]([OH:78])[C@@:73]([O:80][CH3:81])([CH3:79])[CH2:72]2)[C@H:63]([CH3:82])[C@@H:62]([O:83][C@@H:84]2[O:89][C@H:88]([CH3:90])[CH2:87][C@H:86]([N:91]([CH3:92])[CH3:93])[C@H:85]2[OH:94])[C@:61]2([CH3:95])[O:58][C:57](=[C:59]([CH3:97])[CH2:60]2)[C@H:56]([CH3:98])[C@@H:55]([OH:99])[C@@:54]1([OH:101])[CH3:100]

참가 물질

5

반응물 3

HCID 12560ErythromycinHCID 516892Sodium BicarbonateHCID 9875064Erythromycin - Impurity F

생성물 1

HCID 83954Erythromycin A enol ether

시약·촉매·용매 1

HCID 176Acetic Acid용매

실험 절차

Synthesis of EM701 was disclosed in detail in WO 02/14338 A1. A glacial acetic acid solution of erythromycin was stirred at room temperature for 2 hours, and aqueous sodium hydrogencarbonate solution was slowly added and neutralized. The reaction mixture was extracted with chloroform. The organic layer was dehydrated by adding anhydrous sodium sulfate, which was removed off by filtration to obtain crude product. The crude product was purified by silica gel column chromatography with chloroform-methanol-aqueous ammonia (10:0.5:0.01→10:1:0.05) to obtain erythromycin A enol ether. Potassium carbonate was added to methanol solution of erythromycin A enol ether and refluxed for 2 hours. After solvent was removed, the residue was dissolved in aqueous sodium hydrogencarbonate and the mixture was extracted with chloroform. The extract was dehydrated with sodium sulfate, filtered and distilled off. The obtained crude product was purified by silica gel column chromatography with chloroform-methanol-aqueous ammonia (10:0.5:0.01→10:1:0.05) to obtain EM701 (white powder).

후처리

  1. extractionThe reaction mixture was extracted with chloroform
  2. additionby adding anhydrous sodium sulfate, which
  3. customwas removed off by filtration
  4. customto obtain crude product
  5. customThe crude product was purified by silica gel column chromatography with chloroform-methanol-aqueous ammonia (10:0.5:0.01→10:1:0.05)

출처 및 근거

ORD 기록
ord-20f04dbbc9e74f7280d839e3ca439e37
출처 데이터셋
uspto-grants-2009_04
특허 번호
US07521428B2

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