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

HRID 2219864Notes

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.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

Conditions

Temperature: 50 °C

Procedure

Fluvastatin methyl ester (8.0 g) was dissolved in acetone (120 ml) and a solution of NaOH (0.75 g) in MeOH (8 ml) was added. The mixture was heated to 50° C. for 4.25 h, cooled to room temperature and stirred over night. NaOH (0.2 g) was added and the mixture was heated again to 50° C. After 5.5 h a solution of NaOH (0.2 g) in MeOH (8 ml) was added and stirred for 1.5 h, then the mixture was cooled to room temperature and stirred for 1 h. The product was isolated by filtration under nitrogen, washed with acetone (100 ml) and dried at 50° C. in a vacuum oven for 21.5 h to obtain 7.26 g of fluvastatin sodium Form CI.

Workup

temperaturecooled to room temperature
temperaturethe mixture was heated again to 50° C
stirringstirred for 1.5 h
temperaturethe mixture was cooled to room temperature
stirringstirred for 1 h
customThe product was isolated by filtration under nitrogen
washwashed with acetone (100 ml)
customdried at 50° C. in a vacuum oven for 21.5 h

Sources & evidence

ORD record: ord-7c6e58da684b48a9b6ca14cbd0987919
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414140B2

Reaction notes

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