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

HRID 2219859Notes

Reaction equation

HRID 2219859 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]>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+: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 12.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml round bottom flask was loaded with Fluvastatin methyl ester (3.0 g, 7.08 mmole), water (30 ml) and NaOH (0.29 g). The mixture was stirred for 3 h at room temperature then extracted with ethyl acetate (30 ml). The aqueous solution was evaporated, acetonitrile (12 ml) was added and the mixture was stirred at room temperature over night. The product was isolated by filtration under nitrogen flow, washed with acetonitrile (20 ml) and dried at 40° C. in a vacuum oven for 24 h to obtain 0.37 g (12%) of fluvastatin sodium crystal Form LXXVIII.

Workup

  1. extractionthen extracted with ethyl acetate (30 ml)
  2. customThe aqueous solution was evaporated
  3. additionacetonitrile (12 ml) was added
  4. stirringthe mixture was stirred at room temperature over night
  5. customThe product was isolated by filtration under nitrogen flow
  6. washwashed with acetonitrile (20 ml)
  7. customdried at 40° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-c9915f67a3cd4aa0bbe473d3b9da16d6
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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