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

HRID 2247104Notes

Reaction equation

HRID 2247104 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].CC(C)=O.[OH-].[Na+:37]>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+:37]

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 80.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was added to acetone (30 ml) and the solution was stirred at room temperature. NaOH (1 eq.) in EtOH (3 ml) was added to the solution. The mixture was stirred overnight. The product that precipitated was isolated by filtration under nitrogen, washed with acetone (100 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 2.45 g (80.8%) of fluvastatin sodium Form XLIV.

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe product that precipitated
  3. customwas isolated by filtration under nitrogen
  4. washwashed with acetone (100 ml)
  5. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-c5e1478aeba6440ab115ba5327764aaf
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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