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

HRID 2247121Notes

Reaction equation

HRID 2247121 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].C1CCCCC1.[OH-].[Na+:39]>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+:39]

Participants

5

Reactant 3

HCID 8078Cyclohexane2×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 93%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In a 3 neck flask were placed fluvastatin methyl ester (3.0 g) and cyclohexane (60 ml) then the mixture was heated to reflux. A solution of NaOH (0.29 g) in MeOH (3 ml) was added and the mixture was stirred at reflux for 1.6 h. The slurry was cooled to room temperature, cyclohexane (40 ml) was added and the mixture was stirred over night. The product was isolated by filtration under nitrogen, washed with cyclohexane (90 ml) and dried at 50EC in a vacuum oven for 24 h to obtain 2.81 g (93%) of fluvastatin sodium Form XCVII.

Workup

  1. temperaturethe mixture was heated to reflux
  2. temperatureat reflux for 1.6 h
  3. stirringthe mixture was stirred over night
  4. customThe product was isolated by filtration under nitrogen
  5. washwashed with cyclohexane (90 ml)
  6. customdried at 50EC in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-1700ae9977b04faeab239116d5ee82a6
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

Loading…