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

HRID 2219836Notes

Reaction equation

HRID 2219836 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]>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

4

Reactant 2

HCID 14798Sodium HydroxideHCID 13741557Fluvastatin methyl ester

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was added to a solution of NaOH (1 eq.) in MeOH (30 ml). The mixture was stirred at room temperature for 4.5 h. Then, it was filtered and concentration by vacuum distillation until a solid appeared. The concentrated solution was heated to reflux and 60 ml of acetonitrile was dripped into the mixture over 50 min. Turbidity was observed and the mixture was cooled slowly to room temperature and stirred over night. The product was isolated by filtration under nitrogen, washed with acetonitrile (60 ml) and dried at 50° C. in a vacuum oven for 24 h to obtain fluvastatin sodium Form VII (2.54 g, 83.1%).

Workup

  1. filtrationThen, it was filtered
  2. concentrationconcentration
  3. distillationby vacuum distillation until a solid
  4. temperatureThe concentrated solution was heated
  5. temperatureto reflux
  6. wait60 ml of acetonitrile was dripped into the mixture over 50 min
  7. temperaturethe mixture was cooled slowly to room temperature
  8. stirringstirred over night
  9. customThe product was isolated by filtration under nitrogen
  10. washwashed with acetonitrile (60 ml)
  11. customdried at 50° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-e3ad591316b341059f10b4372d3b6299
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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