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

HRID 2247125Notes

Reaction equation

HRID 2247125 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 Hydroxide3×HCID 13741557Fluvastatin methyl ester

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoateYield 89.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 887MethanolSolvent2×

Procedure

Fluvastatin methyl ester (8.0 g) was dissolved in acetone (120 ml) and a solution of NaOH (0.75 g) in MeOH (8 ml) was added. The mixture was heated to 50EC for 4.25 h, cooled to room temperature and stirred over night. NaOH (0.2 g) was added and the mixture was heated again to 50EC. After 5.5 h a solution of NaOH (0.2 g) in MeOH (8 ml) was added and stirred for 1.5 h, then the mixture was cooled to room temperature and stirred for 1 h. The product was isolated by filtration under nitrogen, washed with acetone (100 ml) and dried at 50EC in a vacuum oven for 21.5 h to obtain 7.26 g of fluvastatin sodium Form CI.

Workup

  1. temperatureThe mixture was heated to 50EC for 4.25 h
  2. temperaturethe mixture was heated again to 50EC
  3. stirringstirred for 1.5 h
  4. temperaturethe mixture was cooled to room temperature
  5. stirringstirred for 1 h
  6. customThe product was isolated by filtration under nitrogen
  7. washwashed with acetone (100 ml)
  8. customdried at 50EC in a vacuum oven for 21.5 h

Sources & evidence

ORD record
ord-3fb3e3b4336d4b39806a630a4467d05e
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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