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

HRID 2247088Notes

Reaction equation

HRID 2247088 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>[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

4

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 35.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Fluvastatin methyl ester (3.01 g) was dissolved in acetonitrile (60 ml) by heating and NaOH (0.28 g) was added. The mixture was stirred at about 60EC for 1 h, cooled to room temperature, heated again to about 75EC for 2 h, then cooled to room temperature and stirred overnight. The product was isolated by filtration under nitrogen, washed with acetonitrile (40 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 1.07 g (34.9%) of fluvastatin sodium crystal Form I.

Workup

  1. temperatureby heating
  2. temperatureheated again to about 75EC for 2 h
  3. temperaturecooled to room temperature
  4. stirringstirred overnight
  5. customThe product was isolated by filtration under nitrogen
  6. washwashed with acetonitrile (40 ml)
  7. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-2d9a5028265e4e12b28e2de37f322d0b
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

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