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

HRID 2221063Notes

Reaction equation

HRID 2221063 reaction equation
[CH3:1][CH:2]([N:4]1[C:12]([CH:13]=[CH:14][CH:15]([OH:27])[CH2:16][CH:17]([OH:26])[CH2:18][C:19]([O:21]C(C)(C)C)=[O:20])=[C:11]([C:28]2[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=2)[C:10]2[C:5]1=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH3:3].[OH-].[Na+:36].O>CCO>[CH3:3][CH:2]([N:4]1[C:12](/[CH:13]=[CH:14]/[CH:15]([OH:27])[CH2:16][CH:17]([OH:26])[CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:28]2[CH:29]=[CH:30][C:31]([F:34])=[CH:32][CH:33]=2)[C:10]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]1=2)[CH3:1].[Na+:36]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53394872HCID 53394872, compound

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoateYield 77.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 250 ml round bottom flask was loaded with fluvastatin tert-butyl ester (4.0 g, 8.56 mmole), NaOH (0.35 g), water (48 ml) and EtOH (120 ml) which were added gradually till clear solution was obtained. The mixture was stirred for 2.5 h then the EtOH was evaporated. The volume of the water was completed to 8 vol. and the mixture was extracted with EtOAc (2×30 ml). The aqueous solution was evaporated to obtain 6.07 g and ACN (60 ml) was added. The solution was stirred at room temperature over night. The product was isolated by filtration under nitrogen, washed with ACN (20 ml) and dried at 40° C. in a vacuum oven for 24 h to obtain 2.86 g (77.1%) of fluvastatin sodium crystal form LXXX.

Workup

  1. additionwere added gradually till clear solution
  2. customwas obtained
  3. customthe EtOH was evaporated
  4. extractionthe mixture was extracted with EtOAc (2×30 ml)
  5. customThe aqueous solution was evaporated
  6. customto obtain 6.07 g and ACN (60 ml)
  7. additionwas added
  8. stirringThe solution was stirred at room temperature over night
  9. customThe product was isolated by filtration under nitrogen
  10. washwashed with ACN (20 ml)
  11. customdried at 40° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-0d049a95bd434fdaa35367bcd8fbba6f
Source dataset
uspto-grants-2008_05
Patent number
US07368468B2

Reaction notes

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