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

HRID 2247102Notes

Reaction equation

HRID 2247102 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(O)C>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+:33]

Participants

5

Reactant 3

HCID 3776IsopropanolHCID 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 95%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In a 100 ml flask were placed Fluvastatin methyl ester (2.0 g) and a solution of NaOH (0.19 g) in EtOH (5 ml). The mixture was stirred at reflux for 3.5 h and propan-2-ol (40 ml) was added. The slurry was cooled to room temperature and stirred over night. The product was isolated by filtration under nitrogen, washed with propan-2-ol (20 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 1.93 g (95%) of fluvastatin sodium crystal Form XXXIX.

Workup

  1. customIn a 100 ml flask were placed
  2. temperatureat reflux for 3.5 h
  3. stirringstirred over night
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with propan-2-ol (20 ml)
  6. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-6db321746e1546a29908a495ad04431c
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

Loading…