Acetic Anhydride → Erythromycin 2'-acetate

HRID 275266

Reaktionsgleichung

Reaktionsgleichung von HRID 275266
[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]([OH:46])([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].[CH3:52][C:53](OC(C)=O)=[O:54]>C(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[O:44][C:53]([CH3:52])=[O:54])[C@@:11]([OH:46])([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]

Komponenten

4

Edukt 2

HCID 7918Acetic AnhydrideHCID 12560Erythromycin

Produkt 1

HCID 114919Erythromycin 2'-acetate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To erythromycin A (2.674 mmol) dissolved in 100 mL of CH2Cl2 at ambient temperature and then cooled to 0° C. was added 1.1 equivalents of Ac2O (0.28 mL). The reaction mixture was allowed to warm to ambient temperature, stirred for 3 hours and extracted with CH2Cl2. The combined organic extracts were washed once with 8% sodium bicarbonate solution, tarice with water and once with brine, dried over Na2SO4 and concentrated in vacuo to afford the crude product as a white powder. Recrystallization from acetonitrile afforded the title compound.

Aufarbeitung

  1. temperatureto warm to ambient temperature
  2. extractionextracted with CH2Cl2
  3. washThe combined organic extracts were washed once with 8% sodium bicarbonate solution, tarice with water and once with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customto afford the crude product as a white powder
  7. customRecrystallization from acetonitrile

Quellen und Nachweise

ORD-Eintrag
ord-27fb9f6ed5164e3fb2b31006a240004c
Quelldatensatz
uspto-grants-1995_02
Patentnummer
US05393743

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