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

HRID 2247112Notes

Reaction equation

HRID 2247112 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].CC(C)=O>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+:33]

Participants

5

Reactant 3

HCID 180AcetoneHCID 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 43.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was dissolved in MeOH (15 ml) by heating to reflux. NaOH (0.29 g) was added and the clear solution was stirred at reflux for 30 min, then acetone (75 ml) was added. The solution was cooled to room temperature and stirred over night. The product was isolated by filtration under nitrogen, washed with acetone (35 ml) and dried at 50EC in a vacuum oven for 21.5 h to obtain 1.34 g of fluvastatin sodium crystal Form LXV.

Workup

  1. temperatureby heating to reflux
  2. temperatureat reflux for 30 min
  3. stirringstirred over night
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with acetone (35 ml)
  6. customdried at 50EC in a vacuum oven for 21.5 h

Sources & evidence

ORD record
ord-45e7182112a246f0b95b7f6e1fed6d86
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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