Sodium Azide → 3-Aminorifamycin S

HRID 1252502

Reaktionsgleichung

Reaktionsgleichung von HRID 1252502
[N-:1]=[N+]=[N-].[Na+].[CH3:5][C:6]1[C:11]2[O:12][C@:13]3([CH3:53])[O:16][CH:17]=[CH:18][C@H:19]([O:51][CH3:52])[C@@H:20]([CH3:50])[C@@H:21]([O:46][C:47]([CH3:49])=[O:48])[C@H:22]([CH3:45])[C@H:23]([OH:44])[C@H:24]([CH3:43])[C@@H:25]([OH:42])[C@@H:26]([CH3:41])[CH:27]=[CH:28][CH:29]=[C:30]([CH3:40])[C:31]([NH:33][C:34]4[C:38](=[O:39])[C:8](=[C:9]([C:36](=[O:37])[CH:35]=4)[C:10]=2[C:14]3=[O:15])[C:7]=1[OH:54])=[O:32]>CNC=O.C(Cl)Cl>[CH3:41][C@@H:26]1[C@H:25]([OH:42])[C@@H:24]([CH3:43])[C@@H:23]([OH:44])[C@@H:22]([CH3:45])[C@H:21]([O:46][C:47]([CH3:49])=[O:48])[C@H:20]([CH3:50])[C@@H:19]([O:51][CH3:52])[CH:18]=[CH:17][O:16][C@:13]2([CH3:53])[C:14](=[O:15])[C:10]3[C:11]([O:12]2)=[C:6]([CH3:5])[C:7]([OH:54])=[C:8]2[C:38](=[O:39])[C:34](=[C:35]([NH2:1])[C:36]([C:9]=32)=[O:37])[NH:33][C:31](=[O:32])[C:30]([CH3:40])=[CH:29][CH:28]=[CH:27]1

Komponenten

5

Edukt 2

HCID 33557Sodium AzideHCID 6436726Rifamycin S

Produkt 1

HCID 128896223-Aminorifamycin S

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 31254N-MethylformamideLösungsmittel

Versuchsvorschrift

3-amino-4-deoxo-4-imino-rifamycin S, (a) above, is described in U.S. Pat. No. 4,017,481, where it is made by reacting 3-amino-rifamycin S with gaseous ammonia. The reaction is carried out in a solution of tetrahydrofuran at room temperature for 15 hours with further addition of ammonia. The starting material, 3-amino-rifamycin S may obtained as described in U.S. Pat. No. 4,007,169, where it is obtained by reacting sodium azide with rifamycin S. The reaction is carried out in methylformamide at 35° C. for 60 minutes. The reaction mixture is diluted with methylene chloride and washed with water. The aqueous phase contains rifamycin SV which may be oxidized by, for example, nitrous acid to the starting material rifamycin S. The organic phase is washed with water, dried with sodium sulphate and evaporated to yield 3-amino rifamycin S which is recrystallized from 2-methoxy ethanol.

Aufarbeitung

  1. custom4,007,169, where it is obtained
  2. washwashed with water
  3. washThe organic phase is washed with water
  4. dry with materialdried with sodium sulphate
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-603eb44945514faf8a96f031da6b9678
Quelldatensatz
uspto-grants-1988_05
Patentnummer
US04743619

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