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

HRID 2219861Notes

Reaction equation

HRID 2219861 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]>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+: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-enoateYield 31.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was dissolved in a solution of NaOH (0.29 g) in MeOH (7.5 ml) by heating to reflux. The clear solution was stirred at reflux for 85 min and acetonitrile (50 ml) was added. The solution was cooled to room temperature and stirred over night. The product was isolated by filtration under nitrogen, washed with acetonitrile (50 ml) and dried at 50° C. in a vacuum oven for 25.5 h to obtain 0.97 g of fluvastatin sodium Form XCVIII.

Workup

  1. temperatureby heating to reflux
  2. temperatureat reflux for 85 min
  3. stirringstirred over night
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with acetonitrile (50 ml)
  6. customdried at 50° C. in a vacuum oven for 25.5 h

Sources & evidence

ORD record
ord-1b770636bf1e4bb993515cbaa91f8eb4
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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