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

HRID 2247127Notes

Reaction equation

HRID 2247127 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>[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

5

Reactant 2

HCID 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 34.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Fluvastatin methyl ester (5.0 g) was dissolved in acetonitrile (100 ml) by heating. At 50EC a solution of NaOH (1 eq.) in water (1.25 ml) was added and the mixture was stirred at this temperature for 2 h, then cooled to room temperature and stirred over night. The product was isolated by filtration under nitrogen, washed with acetonitrile (30 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 1.75 g (34.5%) of fluvastatin sodium Form CV.

Workup

  1. temperatureby heating
  2. stirringstirred over night
  3. customThe product was isolated by filtration under nitrogen
  4. washwashed with acetonitrile (30 ml)
  5. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-fd8fca10c7694bea9cc2494ffe57ec07
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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