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

HRID 2247105Notes

Reaction equation

HRID 2247105 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].C(#N)C>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+:33]

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-enoateYield 83%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

In a 100 ml flask were placed fluvastatin methyl ester (2.42 g), EtOH (5 ml) and a solution of NaOH (0.23 g) in EtOH (7 ml). The mixture was stirred at reflux for 2.5 h and acetonitrile (50 ml) was added. The slurry was stirred at reflux for another 3 h then cooled to room temperature and stirred over night. The product was isolated by filtration under nitrogen and dried at 50EC in a vacuum oven for 24 h to obtain 2.02 g (83%) of fluvastatin sodium crystal Form XLVI.

Workup

  1. customIn a 100 ml flask were placed
  2. temperatureat reflux for 2.5 h
  3. stirringThe slurry was stirred
  4. temperatureat reflux for another 3 h
  5. stirringstirred over night
  6. customThe product was isolated by filtration under nitrogen
  7. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-e6551ebcf39943ee840c350ea19127be
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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