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

HRID 2219837Notes

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].C(#N)C.[OH-].[Na+:36]>CCO>[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+:36]

Participants

Conditions

Temperature: 40 °C

Procedure

Fluvastatin methyl ester (3.0 g) was added to acetonitrile (60 ml) and the mixture was heating to about 40° C. for dissolution. A solution of NaOH (1 eq.) in EtOH (7.5 ml) was added and turbidity was immediately observed. The mixture then was heated to about 65° C. The mixture was cooled slowly to room temperature and stirred overnight. The product was isolated by filtration under nitrogen, washed with acetonitrile (40 ml) and dried at 50° C. in a vacuum oven for 24 h to obtain fluvastatin sodium Form VII (1.99 g, 64.9%).

Workup

temperatureThe mixture then was heated to about 65° C
temperatureThe mixture was cooled slowly to room temperature
customThe product was isolated by filtration under nitrogen
washwashed with acetonitrile (40 ml)
customdried at 50° C. in a vacuum oven for 24 h

Sources & evidence

ORD record: ord-17e5e406cb5d445b8724a1f6839d7c5a
Source dataset: uspto-grants-2008_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07414140B2

Reaction notes

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