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

HRID 2247111Notes

Reaction equation

HRID 2247111 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].CO.[OH-].[Na+:35]>CC(O)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+:35]

Participants

5

Reactant 3

HCID 887MethanolHCID 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 30.1%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a 100 ml flask were placed Fluvastatin methyl ester (3.0 g), MeOH (20 ml) and NaOH (0.29 g). After a clear solution was obtained propan-2-ol (80 ml) was added and the solution was stirred at room temperature over night. A little precipitation occurred, propan-2-ol (40 ml) was added and the solution was stirred at room temperature for another night. The product was isolated by filtration under nitrogen, washed with acetone (35 ml) and dried at 50EC in a vacuum oven for 22.5 h to obtain 0.92 g of fluvastatin sodium crystal Form LXV.

Workup

  1. customIn a 100 ml flask were placed
  2. additionwas added
  3. customA little precipitation
  4. additionpropan-2-ol (40 ml) was added
  5. stirringthe solution was stirred at room temperature for another night
  6. customThe product was isolated by filtration under nitrogen
  7. washwashed with acetone (35 ml)
  8. customdried at 50EC in a vacuum oven for 22.5 h

Sources & evidence

ORD record
ord-7cf3eb44d7484cbcbdba10800db9f020
Source dataset
uspto-grants-2010_03
Patent number
US07687642B2

Reaction notes

Loading…