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

HRID 2247098Notes

Reaction equation

HRID 2247098 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

5

Reactant 3

HCID 6342AcetonitrileHCID 14798Sodium HydroxideHCID 13741557Fluvastatin methyl ester

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was added to acetonitrile (60 ml) and the mixture was heating to about 40EC 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 65EC. 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 50EC in a vacuum oven for 24 h to obtain fluvastatin sodium Form VII (1.99 g, 64.9%).

Workup

  1. temperaturethe mixture was heating to about 40EC for dissolution
  2. temperatureThe mixture then was heated to about 65EC
  3. customThe product was isolated by filtration under nitrogen
  4. washwashed with acetonitrile (40 ml)
  5. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-5ae15e1ed1d34d9f86876cf813836b47
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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