Acetic Anhydride → Vinblastine

HRID 1706846

Reaction equation

[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

Participants

Reactant 2

HCID 7918Acetic Anhydride

HCID 1970264-Desacetylvinblastine

Product 1

HCID 13342Vinblastine

Procedure

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.

Sources & evidence

ORD record: ord-45cf85c6278c47f8bbe682054793a7ef
Source dataset: uspto-grants-1980_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04209443

Linked notes

Loading…