2-(Methylamino)ethanol → Rifamycin

HRID 1415408

Reaktionsgleichung

Reaktionsgleichung von HRID 1415408
CNCCO.[CH3:6][C:7]1[C:12]2[O:13][C@:14]3([CH3:54])[O:17][CH:18]=[CH:19][C@H:20]([O:52][CH3:53])[C@@H:21]([CH3:51])[C@@H:22]([O:47][C:48]([CH3:50])=[O:49])[C@H:23]([CH3:46])[C@H:24]([OH:45])[C@H:25]([CH3:44])[C@@H:26]([OH:43])[C@@H:27]([CH3:42])[CH:28]=[CH:29][CH:30]=[C:31]([CH3:41])[C:32]([NH:34][C:35]4[C:39](=[O:40])[C:9](=[C:10]([C:37](=[O:38])[CH:36]=4)[C:11]=2[C:15]3=[O:16])[C:8]=1[OH:55])=[O:33]>O1CCOCC1>[CH3:6][C:7]1[C:12]2[O:13][C@@:14]3([CH3:54])[C:15]([C:11]=2[C:10]2[C:37]([OH:38])=[CH:36][C:35]([NH:34][C:32]([C:31]([CH3:41])=[CH:30][CH:29]=[CH:28][C@H:27]([CH3:42])[C@H:26]([OH:43])[C@@H:25]([CH3:44])[C@@H:24]([OH:45])[C@@H:23]([CH3:46])[C@H:22]([O:47][C:48]([CH3:50])=[O:49])[C@H:21]([CH3:51])[C@@H:20]([O:52][CH3:53])[CH:19]=[CH:18][O:17]3)=[O:33])=[C:39]([OH:40])[C:9]=2[C:8]=1[OH:55])=[O:16]

Komponenten

4

Edukt 2

HCID 80162-(Methylamino)ethanolHCID 6436726Rifamycin S

Produkt 1

HCID 6324616Rifamycin

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

10 g (0.13 mol) of N-methylethanolamine are added to a solution of 21 g (0.03 mol) of rifamycin-S in 20 ml of dioxan and the whole heated for 15 minutes on a boiling water bath. The batch is then evaporated to dryness in vacuo and the residue chromatographed on 2kg of silica gel, using chloroform as eluant. In addition to a dark-colored head zone, two strong, yellow-colored bands are observed. The eluate of the more slowly eluted band is evaporated and the residue crystallized from aqueous methanol. After three crystallizations from aqueous methanol there is obtained 3-N-methylethanol-amino)-rifamycin-SV in the form of coarse prisms melting at 218° C (with decomposition.

Aufarbeitung

  1. temperaturethe whole heated for 15 minutes on a boiling water bath
  2. customThe batch is then evaporated to dryness in vacuo
  3. customthe residue chromatographed on 2kg of silica gel
  4. additionIn addition to a dark-colored head zone, two strong
  5. customThe eluate of the more slowly eluted band is evaporated
  6. customthe residue crystallized from aqueous methanol
  7. customAfter three crystallizations from aqueous methanol

Quellen und Nachweise

ORD-Eintrag
ord-c4a699024f8f439d8291345532d8ac06
Quelldatensatz
uspto-grants-1977_01
Patentnummer
US04005077

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