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

HRID 2219850Notes

Reaction equation

HRID 2219850 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 50° C. 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 50° C. in a vacuum oven for 22.5 h

Sources & evidence

ORD record
ord-972d1f40796e4b73aa02030ced8b421c
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

Loading…