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

HRID 2219849Notes

Reaction equation

HRID 2219849 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(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+:35]

Participants

5

Reactant 3

HCID 887Methanol2×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-enoate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

In a 3 neck flask were placed fluvastatin methyl ester (3.0 g) and MeOH (30 ml). The mixture was heated to reflux for dissolution and NaOH (0.42) was added in two portions. Precipitant was appeared at reflux temperature and wasn't dissolved after addition of another 45 ml of MeOH during 4 h. The slurry mixture was cooled to room temperature and stirred over night. The precipitant was dissolved, acetone (150 ml) was added and the mixture was stirred at room temperature for 22 h. 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 1.68 g of fluvastatin sodium crystal Form LXIV.

Workup

  1. temperatureThe mixture was heated
  2. additionwas added in two portions
  3. temperatureat reflux temperature
  4. dissolutionwasn't dissolved
  5. dissolutionThe precipitant was dissolved
  6. stirringthe mixture was stirred at room temperature for 22 h
  7. customThe product was isolated by filtration under nitrogen
  8. washwashed with acetone (35 ml)
  9. customdried at 50° C. in a vacuum oven for 22.5 h

Sources & evidence

ORD record
ord-64f37ac6f51c4f90b7ebed3de7adfb15
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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