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

HRID 2219866Notes

Reaction equation

HRID 2219866 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 50° C. 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 50° C. 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 50° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-74e2d47b6d884e728a48f80ba4ec31cf
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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