Water → 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][CH:15]([OH:27])[CH2:16][CH:17]([OH:26])[CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[C:11]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].O.[OH-].[Na+:37]>CCO>[CH3:3][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[CH:15]([OH:27])[CH2:16][CH:17]([OH:26])[CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH3:1].[Na+:37]Participants
5
Procedure
A 250 ml round bottom flask was loaded with Fluvastatin tert-butyl ester (8.0 g, 17 mmole), water (64 ml), EtOH (160 ml) and NaOH (0.7 g). The mixture was stirred for 43 h then the EtOH was evaporated. Water (53 ml) was added and the mixture was extracted with EtOAc (2×35 ml). The aqueous solution was evaporated to obtain 18 g and ACN (120 ml) was added. The solution was stirred at room temperature over night. The product was isolated by filtration under nitrogen, washed with ACN (20 ml) and dried at 40° C. in a vacuum oven for 24 h to obtain 4.43 g (60%) of fluvastatin sodium crystal form LXXIX.
Workup
- customthe EtOH was evaporated
- additionWater (53 ml) was added
- extractionthe mixture was extracted with EtOAc (2×35 ml)
- customThe aqueous solution was evaporated
- customto obtain 18 g and ACN (120 ml)
- additionwas added
- stirringThe solution was stirred at room temperature over night
- customThe product was isolated by filtration under nitrogen
- washwashed with ACN (20 ml)
- customdried at 40° C. in a vacuum oven for 24 h
Sources & evidence
- ORD record
- ord-39668a90852f498f810e9b36ee8eb24a
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368468B2
Reaction notes
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