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

HRID 2221060Notes

Reaction equation

HRID 2221060 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].O.[OH-].[Na+:34]>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+:34]

Participants

5

Reactant 3

HCID 962WaterHCID 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 65%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 100 ml round bottom flask was loaded with fluvastatin methyl ester (5.0 g, 11.8 mmole), water (15 ml), EtOH (25 ml) and NaOH (0.49 g). The mixture became clear and was stirred for 4.5 h. The EtOH was evaporated, water (completing to 10 vol.) was added and extracted with EtOAc (2×20 ml). The aqueous phase was evaporated, then acetonitrile (70 ml) was added and the mixture was stirred at room temperature over night. The product was isolated by filtration under nitrogen flow, washed with acetonitrile (20 ml) and dried at 40° C. in a vacuum oven for 24 h to obtain 3.31 g (65%) of fluvastatin sodium crystal Form LXXIII.

Workup

  1. customThe EtOH was evaporated
  2. additionwater (completing to 10 vol.) was added
  3. extractionextracted with EtOAc (2×20 ml)
  4. customThe aqueous phase was evaporated
  5. additionacetonitrile (70 ml) was added
  6. stirringthe mixture was stirred at room temperature over night
  7. customThe product was isolated by filtration under nitrogen flow
  8. washwashed with acetonitrile (20 ml)
  9. customdried at 40° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-49e40af2c3af4edfaadb8e0d2eed731b
Source dataset
uspto-grants-2008_05
Patent number
US07368468B2

Reaction notes

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