Sodium Azide → 3-Aminorifamycin S

HRID 435928

Reaktionsgleichung

Reaktionsgleichung von HRID 435928
[CH3:1][C:2]1[C:7]2[O:8][C@:9]3([CH3:49])[O:12][CH:13]=[CH:14][C@H:15]([O:47][CH3:48])[C@@H:16]([CH3:46])[C@@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:18]([CH3:41])[C@H:19]([OH:40])[C@H:20]([CH3:39])[C@@H:21]([OH:38])[C@@H:22]([CH3:37])[CH:23]=[CH:24][CH:25]=[C:26]([CH3:36])[C:27]([NH:29][C:30]4[C:34](=[O:35])[C:4](=[C:5]([C:32](=[O:33])[CH:31]=4)[C:6]=2[C:10]3=[O:11])[C:3]=1[OH:50])=[O:28].[N-:51]=[N+]=[N-].[Na+]>N1CCCC1=O>[CH3:37][C@@H:22]1[C@H:21]([OH:38])[C@@H:20]([CH3:39])[C@@H:19]([OH:40])[C@@H:18]([CH3:41])[C@H:17]([O:42][C:43]([CH3:45])=[O:44])[C@H:16]([CH3:46])[C@@H:15]([O:47][CH3:48])[CH:14]=[CH:13][O:12][C@:9]2([CH3:49])[C:10](=[O:11])[C:6]3[C:7]([O:8]2)=[C:2]([CH3:1])[C:3]([OH:50])=[C:4]2[C:34](=[O:35])[C:30](=[C:31]([NH2:51])[C:32]([C:5]=32)=[O:33])[NH:29][C:27](=[O:28])[C:26]([CH3:36])=[CH:25][CH:24]=[CH:23]1

Komponenten

4

Edukt 2

HCID 33557Sodium AzideHCID 6436726Rifamycin S

Produkt 1

HCID 128896223-Aminorifamycin SAusbeute 22,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 120252-PyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

14 g rifamycin S were dissolved in 70 ml pyrrolidone and added with 2.6 g sodium azide. The solution was heated at 60° C for 15 min., then at 80° C for further 15 min. The reaction mixture was then treated as in Example 3 to obtain 3.2 g 3-amino-rifamycin S identical to that described in Example 3.

Aufarbeitung

  1. additionThe reaction mixture was then treated as in Example 3

Quellen und Nachweise

ORD-Eintrag
ord-0f6a61451eeb44de9f280479b78cbdbc
Quelldatensatz
uspto-grants-1977_02
Patentnummer
US04007169

Verknüpfte Notizen

Wird geladen…