Acetone → sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate
Reaction equation
[CH3:1][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[C@H:15]([OH:24])[CH2:16][C@H:17]([OH:23])[CH2:18][C:19]([O:21]C)=[O:20])=[C:11]([C:25]2[CH:30]=[CH:29][C:28]([F:31])=[CH:27][CH:26]=2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].[OH-].[Na+:33].CC(C)=O>O.CO>[CH3:3][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[CH:15]([OH:24])[CH2:16][CH:17]([OH:23])[CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:25]2[CH:26]=[CH:27][C:28]([F:31])=[CH:29][CH:30]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH3:1].[Na+:33]Participants
6
Procedure
Fluvastatin methyl ester (3.0 g) was added to a solution of NaOH (1 eq.) in water (0.75 ml) and methanol (7.5 ml). The mixture was stirred at about 65EC for 3.5 h. Then, another portion of NaOH (0.5 eq.) in water (0.4 ml) was added. After another 40 min the starting material was no longer detectable by HPLC. Acetone (58 ml) was dripped into the solution over 25 min. Turbidity appeared in the solution. The mixture was cooled slowly to room temperature and stirred overnight. The product was isolated by filtration under nitrogen, washed with acetone (20 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 0.25 g (8.2%) of fluvastatin sodium Form XXX.
Workup
- waitAfter another 40 min the starting material was no longer detectable by HPLC
- stirringstirred overnight
- customThe product was isolated by filtration under nitrogen
- washwashed with acetone (20 ml)
- customdried at 50EC in a vacuum oven for 24 h
Sources & evidence
- ORD record
- ord-6345ccd07e664824b257471c4496767a
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07687642B2
Reaction notes
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