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

HRID 2247093Notes

Reaction equation

HRID 2247093 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.C(O)CCC>[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-enoate

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 962WaterSolvent

Procedure

Fluvastatin methyl ester (2.0 g) was added to a solution of NaOH (1 eq.) in water (0.5 ml) and butan-1-ol (8 ml). The mixture was stirred at about 80EC for 4 h, after which the starting material was not detected by HPLC. Then, acetonitrile (40 ml) was dripped into the solution and the mixture was cooled slowly to room temperature and stirred overnight. The product was isolated by filtration under nitrogen, washed with acetonitrile (15 ml) and dried at 50EC in a vacuum oven for 24 h to obtain fluvastatin sodium Form VI (1.65 g, 81%).

Workup

  1. stirringstirred overnight
  2. customThe product was isolated by filtration under nitrogen
  3. washwashed with acetonitrile (15 ml)
  4. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-89fdd4e6760f4f2883cc0abdfa6ccfda
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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