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

HRID 2247096Notes

Reaction equation

HRID 2247096 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(OC)(C)C>O.CC(O)C>[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

6

Reactant 3

HCID 14798Sodium HydroxideHCID 15413tert-Butyl methyl etherHCID 13741557Fluvastatin methyl ester

Product 1

HCID 16760425sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoateYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent2×

Procedure

Fluvastatin methyl ester (3.0 g) was added to a solution of NaOH (1 eq.) in water (0.75 ml) and propan-2-ol (7.5 ml). The mixture was heated to reflux and 1 ml of propan-2-ol was added. After 2 h the mixture was cooled to room temperature and stirred for 2 h. MTBE (60 ml) was dripped into the solution over 20 min and it was stirred for another 1.5 h. The product was isolated by filtration under nitrogen, washed with MTBE and dried at 50EC in a vacuum oven for 24 h to obtain 1.9 g (62%) of fluvastatin sodium Form VII.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. stirringit was stirred for another 1.5 h
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with MTBE
  6. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-105b35806a7340989bad5394dfbf6dbb
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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