Fumaric Acid → Fesoterodine fumarate
Reaction equation
[CH3:1][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:22])[CH3:21])[CH:17]([CH3:19])[CH3:18])=[O:5])[CH3:3].[C:31]([OH:38])(=[O:37])/[CH:32]=[CH:33]/[C:34]([OH:36])=[O:35]>O>[CH3:3][CH:2]([C:4]([O:6][C:7]1[CH:8]=[CH:9][C:10]([CH2:29][OH:30])=[CH:11][C:12]=1[C@@H:13]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:14][CH2:15][N:16]([CH:20]([CH3:21])[CH3:22])[CH:17]([CH3:18])[CH3:19])=[O:5])[CH3:1].[CH:32](/[C:31]([OH:38])=[O:37])=[CH:33]\[C:34]([OH:36])=[O:35]Participants
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 40 °C
Procedure
15.1 g (36.6 mmols) of fesoterodine are loaded into a 1 liter flask, followed by 4.25 g (36.6 mmols) of fumaric acid and 450 ml of deionised water. The mixture is stirred at 40° C. until complete dissolution of the solids and filtered over a 0.45 micron filter. The solution is then divided in equal parts and loaded into three 1000 ml flasks. Each flask is connected to a rotavapor without activating the vacuum and under rotation each flask is immersed in a dry ice and acetone bath kept at −50° C. Each flask is left in such conditions for two hours, until a uniform layer of frozen material is obtained on the inner surface of each flask. The three flasks are then connected to a lyophilisation apparatus CHRIST Alpha 1-4 LSC and their content is lyophilized. The conditions used were the following:
Workup
- filtrationfiltered over a 0.45 micron
- filtrationfilter
- customEach flask is connected to a rotavapor
- customkept at −50° C
- customis obtained on the inner surface of each flask
Sources & evidence
- ORD record
- ord-19a5964de504497dbb99d127fabe6eac
- Source dataset
- uspto-grants-2011_11
- Patent number
- US08049031B2
Reaction notes
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