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

HRID 2247099Notes

Reaction equation

HRID 2247099 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].CCO.[OH-].[Na+:36].CC(O)C>O>[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+:36]

Participants

6

Reactant 4

HCID 702EthanolHCID 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 63.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Into a 100 ml flask were placed fluvastatin methyl ester (3.0 g), EtOH (7.5 ml) and a solution of NaOH (0.28 g) in water (0.75 ml). The mixture was heated to reflux for two h, propan-2-ol was added (58 ml) and the mixture was cooled to room temperature and stirred over night. The product was isolated by filtration under nitrogen, washed with propan-2-ol (50 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 1.92 g (62.8%) of fluvastatin sodium crystal Form IX.

Workup

  1. customInto a 100 ml flask were placed
  2. temperatureThe mixture was heated
  3. additionwas added (58 ml)
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with propan-2-ol (50 ml)
  6. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-40a3855dc136414b85f45a04f2ef51d1
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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