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

HRID 2247090Notes

Reaction equation

HRID 2247090 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].C(#N)C>O.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

6

Reactant 3

HCID 6342AcetonitrileHCID 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 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

Fluvastatin methyl ester (3.0 g) was added to a solution of NaOH (1 eq.) in water (0.75 ml) and methanol (7.5 ml). The mixture was stirred at about 60EC for 4 hr, after which the starting material was no longer detectable by HPLC. Then, acetonitrile (58 ml) was dripped into the solution over 1.5 h. Turbidity appeared in the solution which as it was allowed to cool slowly to room temperature. The mixture was stirred overnight. The product was isolated by filtration under nitrogen, washed with acetonitrile (50 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 2.23 g (73%) of fluvastatin sodium Form VI.

Workup

  1. stirringThe mixture was stirred overnight
  2. customThe product was isolated by filtration under nitrogen
  3. washwashed with acetonitrile (50 ml)
  4. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-f88b05d12c22487fb6dd5ece7e78850a
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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