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

HRID 2247109Notes

Reaction equation

HRID 2247109 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 81.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was added to acetonitrile (60 ml) and dissolved by heating the mixture to reflux. The solution was then cooled to about 40EC and NaOH (1 eq.) dissolved in MeOH (7.5 ml) was added. Turbidity appeared immediately. After 30 minutes an oil residue separated from the mixture. The mixture was heated again to about 55EC for 3 h to dissolve the oil. 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 2.48 g (81.1%) of fluvastatin sodium Form LV.

Workup

  1. dissolutiondissolved
  2. temperatureby heating the mixture
  3. temperatureto reflux
  4. additionwas added
  5. customAfter 30 minutes an oil residue separated from the mixture
  6. temperatureThe mixture was heated again to about 55EC for 3 h
  7. dissolutionto dissolve the oil
  8. customThe product was isolated by filtration under nitrogen
  9. washwashed with acetonitrile (40 ml)
  10. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-19d4d219cb7d4865befdc4f26470953e
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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