Erythromycin → Erythromycin A enol ether

HRID 1093928

반응식

HRID 1093928 반응식
[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:43])[CH3:42])[C@H:35]2[OH:44])[C@@:11](O)([CH3:45])[CH2:10][C@@H:9]([CH3:47])[C:7](=[O:8])[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50].C([O-])(O)=O.[Na+]>C(O)(=O)C.C(Cl)(Cl)Cl>[CH3:1][CH2:2][C@H:3]1[O:18][C:16](=[O:17])[C@H:15]([CH3:19])[C@@H:14]([O:20][C@@H:21]2[O:26][C@@H:25]([CH3:27])[C@H:24]([OH:28])[C@@:23]([O:30][CH3:31])([CH3:29])[CH2:22]2)[C@H:13]([CH3:32])[C@@H:12]([O:33][C@@H:34]2[O:39][C@H:38]([CH3:40])[CH2:37][C@H:36]([N:41]([CH3:42])[CH3:43])[C@H:35]2[OH:44])[C@:11]2([CH3:45])[O:8][C:7](=[C:9]([CH3:47])[CH2:10]2)[C@H:6]([CH3:48])[C@@H:5]([OH:49])[C@@:4]1([OH:51])[CH3:50]

참가 물질

5

반응물 2

HCID 12560ErythromycinHCID 516892Sodium Bicarbonate

생성물 1

HCID 83954Erythromycin A enol ether수율 71%

시약·촉매·용매 2

HCID 176Acetic Acid용매HCID 6212Chloroform용매

실험 절차

A solution (710.0 mL) of EMA (erythromycin A; 104.4 g, 16.90 mmol) in glacial acetic acid was stirred at room temperature for 2 hr, and aqueous NaHCO3 solution was slowly added to neutralize the solution. The reaction mixture was extracted with CHCl3, and the organic layer was dried over Na2SO4. The residue was filtrated, and the filtrate was concentrated to give a crude product (99.30 g). The obtained crude product was dissolved in CHCl3 (250 mL), and the solution was recrystallized by adding hexane (50 mL) to give EM201 (74.50 g, 71%) as a white powder.

후처리

  1. extractionThe reaction mixture was extracted with CHCl3
  2. dry with materialthe organic layer was dried over Na2SO4
  3. filtrationThe residue was filtrated
  4. concentrationthe filtrate was concentrated
  5. customto give a crude product (99.30 g)
  6. customThe obtained crude product
  7. customthe solution was recrystallized
  8. additionby adding hexane (50 mL)

출처 및 근거

ORD 기록
ord-ff43884e357a450f8db78c46fb556a21
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08133871B2

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