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

HRID 2247116Notes

Reaction equation

HRID 2247116 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 2

HCID 14798Sodium Hydroxide2×HCID 13741557Fluvastatin methyl ester

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoateYield 90.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was dissolved in acetone (45 ml) and a solution of NaOH (0.44 g) in MeOH (6 ml) was added. After 29 h, NaOH (0.14 g) was added and the mixture was stirred at room temperature for another 1 h, then it was cooled with ice bath for 30 min. The product was isolated by filtration under nitrogen, washed with acetone (38 ml) and dried at 50EC in a vacuum oven for 22 h to obtain 2.76 g of fluvastatin sodium crystal Form LXVIII.

Workup

  1. temperatureit was cooled with ice bath for 30 min
  2. customThe product was isolated by filtration under nitrogen
  3. washwashed with acetone (38 ml)
  4. customdried at 50EC in a vacuum oven for 22 h

Sources & evidence

ORD record
ord-ddb84bfd56f441e584f8ce874956f83d
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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