Sodium Hydroxide → sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate

HRID 2221062Notes

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].[OH-].[Na+:36]>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+:36]

Participants

Conditions

Temperature: 50 °C

Procedure

A 100 ml round bottom flask was loaded with fluvastatin tert-butyl ester (2.0 g, 4.28 mmole), EtOH (20 ml) and NaOH (0.18 g). The mixture was heated to 50° C. and stirred for 2.25 h then cooled to room temperature and the EtOH was evaporated. The volume of the water was completed to 8 vol. and the mixture was extracted with EtOAc (2×20 ml). The aqua solution was evaporated to obtain 4.22 g and ACN (30 ml) was added. The solution was stirred at room temperature over the weekend. 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 1.15 g (62%) of fluvastatin sodium crystal form LXXIX.

Workup

temperaturethen cooled to room temperature
customthe EtOH was evaporated
extractionthe mixture was extracted with EtOAc (2×20 ml)
customThe aqua solution was evaporated
customto obtain 4.22 g and ACN (30 ml)
additionwas added
stirringThe solution was stirred at room temperature over the weekend
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-23f60e9b356046ffb03d335aba6d8eab
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07368468B2

Reaction notes

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