Acetic Anhydride → Vinblastine

HRID 1706846

Reaktionsgleichung

[CH3:1][CH2:2][C@@:3]1([OH:56])[CH2:14][N:12]2[CH2:13][C@@H:5]([CH2:6][C@:7]([C:52]([O:54][CH3:55])=[O:53])([C:22]3[CH:27]=[C:26]4[C:28]56[C@@H:39]([N:40]([CH3:41])[C:25]4=[CH:24][C:23]=3[O:50][CH3:51])[C@@:38]([OH:46])([C:42]([O:44][CH3:45])=[O:43])[C@H:37]([OH:47])[C@:33]3([CH2:48][CH3:49])[CH:34]=[CH:35][CH2:36][N:31]([C@H:32]53)[CH2:30][CH2:29]6)[C:8]3[NH:21][C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:9]=3[CH2:10][CH2:11]2)[CH2:4]1.[C:57](OC(=O)C)(=[O:59])[CH3:58]>>[CH3:1][CH2:2][C@@:3]1([OH:56])[CH2:14][N:12]2[CH2:13][C@H:5]([CH2:6][C@:7]([C:52]([O:54][CH3:55])=[O:53])([C:22]3[CH:27]=[C:26]4[C@:28]56[C@@H:32]7[C@:33]([CH2:48][CH3:49])([C@@H:37]([O:47][C:57]([CH3:58])=[O:59])[C@:38]([OH:46])([C:42]([O:44][CH3:45])=[O:43])[C@@H:39]5[N:40]([CH3:41])[C:25]4=[CH:24][C:23]=3[O:50][CH3:51])[CH:34]=[CH:35][CH2:36][N:31]7[CH2:30][CH2:29]6)[C:8]3[NH:21][C:20]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[C:9]=3[CH2:10][CH2:11]2)[CH2:4]1

Komponenten

Edukt 2

HCID 7918Acetic Anhydride

HCID 1970264-Desacetylvinblastine

Produkt 1

HCID 13342Vinblastine

Versuchsvorschrift

0.29 g of deacetyl-vinblastine is dissolved in 3 ml of acetic anhydride and the solution is allowed to stand for one hour at room temperature. The thus obtained vinblastine is isolated from the reaction mixture in the usual way and then converted into the sulfate salt. 0.28 g of vinblastine sulfate is obtained.

Quellen und Nachweise

ORD-Eintrag: ord-45cf85c6278c47f8bbe682054793a7ef
Quelldatensatz: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US04209443

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