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

HRID 2219858Notes

Reaction equation

HRID 2219858 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 31.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A 100 ml round bottom flask was loaded with fluvastatin methyl ester (4.0 g, 9.4 mmole), water (32 ml) and NaOH (0.39 g). The mixture was stirred for 3 days at room temperature then extracted with ethyl acetate (32 ml, 16 ml). The aqueous solution was evaporated, propan-2-ol (40 ml) was added and the mixture was stirred at room temperature over night. Precipitation occurred after scraping the mixture with spatula and stirring for another day. The product was isolated by filtration under nitrogen flow, washed with propan-2-ol (20 ml) and dried at 50° C. in a vacuum oven for 24 h to obtain 1.28 g (31%) of fluvastatin sodium crystal Form LXXVIII.

Workup

  1. extractionthen extracted with ethyl acetate (32 ml, 16 ml)
  2. customThe aqueous solution was evaporated
  3. additionpropan-2-ol (40 ml) was added
  4. stirringthe mixture was stirred at room temperature over night
  5. customPrecipitation
  6. stirringstirring for another day
  7. customThe product was isolated by filtration under nitrogen flow
  8. washwashed with propan-2-ol (20 ml)
  9. customdried at 50° C. in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-f6a1beb013ec439cbf49919e510bb4d7
Source dataset
uspto-grants-2008_08
Patent number
US07414140B2

Reaction notes

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