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

HRID 2247122Notes

Reaction equation

HRID 2247122 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 50EC 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 50EC in a vacuum oven for 25.5 h

Sources & evidence

ORD record
ord-54ef5f0c996d446a9d9b08cbbff7b011
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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