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

HRID 2219855Notes

Reaction equation

HRID 2219855 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 50° C. 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 50° C. in a vacuum oven for 22 h

Sources & evidence

ORD record
ord-a072c4d1b960453b84bc4a4b3ad324f9
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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