Erythromycin → Erythromycin A enol ether

HRID 1093928

Reaction equation

HRID 1093928 reaction equation
[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]

Participants

5

Reactant 2

HCID 12560ErythromycinHCID 516892Sodium Bicarbonate

Product 1

HCID 83954Erythromycin A enol etherYield 71%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6212ChloroformSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ff43884e357a450f8db78c46fb556a21
Source dataset
uspto-grants-2012_03
Patent number
US08133871B2

Linked notes

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