Hydrochloric Acid → HCID 22261973, compound

HRID 1610532Notes

Reaction equation

HRID 1610532 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:30])[CH:9]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[C:18]([O:23][C:24]([F:29])([F:28])[CH:25]([F:27])[F:26])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 22261567HCID 22261567, compound

Product 1

HCID 22261973HCID 22261973, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl(2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-methyl-3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionate (4.5 g, 10.4 mmol) in methanol (20 ml) was added 2N aqueous sodium hydroxide solution (10.4 ml, 20.8 mmol), and the mixture was stirred overnight at room temperature. The reaction solution was acidified with 1N hydrochloric acid and extracted with ethyl acetate (200 ml×2). The extract was washed with water and saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from diethyl ether-hexane to give (2RS,3RS)-3-(4-fluorophenyl)-3-hydroxy-2-((4-methyl-3-((1,1,2,2-tetrafluoroethyl)oxy)phenyl)methyl)propionic acid (3.56 g, 85%).

Workup

  1. extractionextracted with ethyl acetate (200 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from diethyl ether-hexane

Sources & evidence

ORD record
ord-c38b1fb5802f41d9a3032e2260b49a8b
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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