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]>C1COCC1>[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 1 liter reactor was loaded with Fluvastatin tert-butyl ester (70 g, 0.15 mole), water (576 ml), THF (280 ml) and NaOH (6 g). After 2 h THF (35 ml) was added and the mixture was stirred for another 9.5 h. The solution was extracted with ethyl acetate (2×200 ml). The aqueous phase was distilled and acetonitrile (1050 ml) was added and the mixture was stirred at room temperature over night. The product was isolated by filtration under nitrogen flow, washed with acetonitrile and dried at 40° C. in a vacuum oven for 24 h to obtain 50.4 g (77.6%) of fluvastatin sodium crystal Form LXXIII (water content: 5.9% wt. % by KF, LOD by TGA 6.0 wt. %).
Workup
- extractionThe solution was extracted with ethyl acetate (2×200 ml)
- distillationThe aqueous phase was distilled
- additionacetonitrile (1050 ml) was added
- stirringthe mixture was stirred at room temperature over night
- customThe product was isolated by filtration under nitrogen flow
- washwashed with acetonitrile
- customdried at 40° C. in a vacuum oven for 24 h
Sources & evidence
- ORD record
- ord-131768dc631c4675845158cd50232fec
- Source dataset
- uspto-grants-2008_05
- Patent number
- US07368468B2
Reaction notes
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